NP-MRD: Showing NP-Card for Burkinabin A (NP0074383)

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Record Information

Version

2.0

Created at

2022-04-28 19:32:58 UTC

Updated at

2022-04-28 19:32:58 UTC

NP-MRD ID

NP0074383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Burkinabin A

Description

Burkinabin A belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. Burkinabin A is found in Fagara zanthoxyloides and Zanthoxylum zanthoxyloides. Burkinabin A was first documented in 2009 (PMID: 19110407). Based on a literature review very few articles have been published on Burkinabin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221322D          

 35 37  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499   -1.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118   -1.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -1.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
  4 31  1  6  0  0  0
  2 32  1  6  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  2 35  1  1  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -4.7188    4.0985    1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421    3.8854   -0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8071    2.7753   -0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2553    1.8906    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5264    0.7891   -0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465   -0.1411    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.0816    1.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -1.2432    0.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -2.1542    1.3151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3552   -3.4451    1.1220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4012   -3.5749    2.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4843   -4.6684    1.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -4.4960    0.2016 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0087   -4.2600   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -5.7538    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041   -6.4336   -0.8598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -6.2120    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -3.3895    0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227   -2.1399    1.1052 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2223   -1.0914    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0021   -0.0168    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587    0.0048    1.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4201    1.0456   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    1.0371   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477    2.0731   -2.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336    3.1061   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263    4.1331   -2.8140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    3.1202   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3992    4.1631   -0.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7994    4.1776    1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1958    2.0825    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    0.5975   -1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    1.4651   -2.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328    2.5648   -2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849    3.4497   -3.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8061    4.4973    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5106    4.8995    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    3.1988    1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3942    2.0600    1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -1.7707    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287   -3.5359    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919   -3.5658    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954   -5.5541    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0298   -4.6681    2.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2426   -3.3732   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -7.1976    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -3.1953   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159   -3.8360    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2901   -1.8385    2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.2662   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492    2.0675   -3.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463    4.1192   -3.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    4.0850    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4475    3.2837    1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3380    5.1270    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    2.1420    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7819   -0.2834   -1.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721    1.3057   -3.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128    4.2461   -2.7295 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
  4  5  1  0
  5 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  6
 13 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 31  2  0
 31 28  1  0
 28 29  1  0
 29 30  1  0
 28 26  2  0
 26 27  1  0
 26 25  1  0
 25 24  2  0
 13 15  1  0
 15 17  1  0
 15 16  2  0
 34  3  1  0
 19  9  1  0
 24 23  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
 32 57  1  0
 33 58  1  0
 35 59  1  0
  9 40  1  1
 10 41  1  6
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  1
 31 56  1  0
 30 53  1  0
 30 54  1  0
 30 55  1  0
 27 52  1  0
 25 51  1  0
 24 50  1  0
 17 46  1  0
M  END


  Mrv1652304282221322D          

 35 37  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499   -1.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118   -1.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -1.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
  4 31  1  6  0  0  0
  2 32  1  6  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  2 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)O[C@H]1[C@H](O)C[C@@](O)(C[C@H]1OC(=O)C1=CC(OC)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O12/c1-32-16-7-11(3-5-13(16)24)20(27)34-18-10-23(31,22(29)30)9-15(26)19(18)35-21(28)12-4-6-14(25)17(8-12)33-2/h3-8,15,18-19,24-26,31H,9-10H2,1-2H3,(H,29,30)/t15-,18-,19+,23-/m1/s1

> <INCHI_KEY>
NNIPMYIDMKBMBF-JYISGYRJSA-N

> <FORMULA>
C23H24O12

> <MOLECULAR_WEIGHT>
492.433

> <EXACT_MASS>
492.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.835956233724175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4S,5R)-1,3-dihydroxy-4,5-bis(4-hydroxy-3-methoxybenzoyloxy)cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.37283669

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.686597024890789

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.739882201866058

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246892587263626

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
116.23739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4S,5R)-1,3-dihydroxy-4,5-bis(4-hydroxy-3-methoxybenzoyloxy)cyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.723  -3.260   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.093  -1.954   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.262  -3.207   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.723  -3.260   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32   35                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
CONECT   17   12   18                                                       
CONECT   18   17                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31    4                                                            
CONECT   32    2   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₁₂

Average Mass

492.4330 Da

Monoisotopic Mass

492.12678 Da

IUPAC Name

(1R,3R,4S,5R)-1,3-dihydroxy-4,5-bis(4-hydroxy-3-methoxybenzoyloxy)cyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S,5R)-1,3-dihydroxy-4,5-bis(4-hydroxy-3-methoxybenzoyloxy)cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(=O)O[C@H]1[C@H](O)C[C@@](O)(C[C@H]1OC(=O)C1=CC(OC)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C23H24O12/c1-32-16-7-11(3-5-13(16)24)20(27)34-18-10-23(31,22(29)30)9-15(26)19(18)35-21(28)12-4-6-14(25)17(8-12)33-2/h3-8,15,18-19,24-26,31H,9-10H2,1-2H3,(H,29,30)/t15-,18-,19+,23-/m1/s1

InChI Key

NNIPMYIDMKBMBF-JYISGYRJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Fagara zanthoxyloides	Plant	KNApSAcK
Zanthoxylum zanthoxyloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Alkyl aryl ether
Alpha-hydroxy acid
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.63	ALOGPS
logP	1.37	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.24 m³·mol⁻¹	ChemAxon
Polarizability	46.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00035543

Chemspider ID

10363135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23250812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ouattara B, Jansen O, Angenot L, Guissou IP, Frederich M, Fondu P, Tits M: Antisickling properties of divanilloylquinic acids isolated from Fagara zanthoxyloides Lam. (Rutaceae). Phytomedicine. 2009 Mar;16(2-3):125-9. doi: 10.1016/j.phymed.2008.10.013. Epub 2008 Dec 24. [PubMed:19110407 ]

Showing NP-Card for Burkinabin A (NP0074383)

MOL for NP0074383 (Burkinabin A)

3D MOL for NP0074383 (Burkinabin A)

3D SDF for NP0074383 (Burkinabin A)

3D-SDF for NP0074383 (Burkinabin A)

PDB for NP0074383 (Burkinabin A)

3D PDB for NP0074383 (Burkinabin A)

SMILES for NP0074383 (Burkinabin A)

INCHI for NP0074383 (Burkinabin A)

Structure for NP0074383 (Burkinabin A)

3D Structure for NP0074383 (Burkinabin A)