NP-MRD: Showing NP-Card for Isobongkrekic acid, (NP0004618)

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Record Information

Version

1.0

Created at

2020-12-09 02:03:39 UTC

Updated at

2021-07-15 16:49:40 UTC

NP-MRD ID

NP0004618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isobongkrekic acid,

Provided By

NPAtlas

Description

Bongkrekic acid is also known as bongkrekate. Bongkrekic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Isobongkrekic acid, is found in Burkholderia gladioli and Pseudomonas. It was first documented in 1976 (PMID: 1276139). Based on a literature review a significant number of articles have been published on bongkrekic acid (PMID: 12034471) (PMID: 15919152) (PMID: 17123460) (PMID: 20237660).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118083D          

 73 72  0  0  0  0            999 V2000
   -4.4099   -2.2890    2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8893   -1.1118    2.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.1925    1.5317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2452    1.0235    1.7115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5034    2.0268    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    2.4079   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231    1.8908   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185    2.3128   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4235    0.7908   -0.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -8.0648    1.1308    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6067    0.3276    3.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
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 32 70  1  0  0  0  0
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 32 72  1  0  0  0  0
 35 73  1  0  0  0  0
M  END

     RDKit          3D

 73 72  0  0  0  0  0  0  0  0999 V2000
   -4.4099   -2.2890    2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8893   -1.1118    2.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  1
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 17 59  1  0
 19 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 30 69  1  0
 32 70  1  0
 32 71  1  0
 32 72  1  0
 35 73  1  0
M  END


  Mrv1652306242118083D          

 73 72  0  0  0  0            999 V2000
   -4.4099   -2.2890    2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8893   -1.1118    2.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.1925    1.5317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2452    1.0235    1.7115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5034    2.0268    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    2.4079   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231    1.8908   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185    2.3128   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    1.8206   -1.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4235    0.7908   -0.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8635    0.4555   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657   -0.7114   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806   -1.0479   -0.7670 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7432    0.0817   -0.6681 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4321    1.1010   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1258   -0.4525   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320   -0.3010    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4114   -0.8333   -0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2668   -0.6722    0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0094   -0.0080    2.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9438    0.4973    2.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0496    0.0892    3.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7038   -1.5138   -1.2786 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0076   -2.0701   -1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2600   -2.4945   -2.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0638   -2.2346   -0.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5479    0.3199    1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9602    0.9879    2.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4189    0.2333    0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0781   -0.3858   -0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0130   -0.4450   -1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3403    0.1241   -1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7457   -1.0534   -2.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6136   -1.1071   -3.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4776   -1.5808   -3.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -1.9926    1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1301   -2.9780    2.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1230   -2.7387    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5503    1.4820    2.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5192    2.4502    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8183    3.1488   -0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6186    3.0540   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    1.4248   -2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424    2.6810   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1808    1.0386    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1526   -0.1432   -0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469    1.2968   -0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503   -1.5442   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8771   -1.5657   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311   -1.8697   -0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    0.6267    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    0.8893   -2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2802    1.1328   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830    2.1138   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4123   -0.9579   -1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786    0.2000    0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3121   -1.0650    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1663    0.9965    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400   -0.7189   -2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9013   -2.2811   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3401   -3.1305   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0648    1.1308    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6067    0.3276    3.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041    1.9783    2.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4239    0.6343    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1355   -0.8222   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2234    1.2128   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8359   -0.3309   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2675   -2.5603   -2.9340 H   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
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 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
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 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  3 39  1  6  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  0  0  0  0
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 14 54  1  1  0  0  0
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 19 60  1  0  0  0  0
 22 61  1  0  0  0  0
 23 62  1  0  0  0  0
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 32 71  1  0  0  0  0
 32 72  1  0  0  0  0
 35 73  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/C(/[H])=C(\[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C(\[H])=C(/[H])C([H])([H])C([H])([H])C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])[C@@]([H])(OC([H])([H])[H])C(=C(\[H])/C(/[H])=C(/C(=O)O[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1

> <INCHI_KEY>
SHCXABJSXUACKU-WUTQZGRKSA-N

> <FORMULA>
C28H38O7

> <MOLECULAR_WEIGHT>
486.605

> <EXACT_MASS>
486.261753564

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.96134853127275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
5.495726164333333

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.641428927807734

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.070980916830315

> <JCHEM_PKA_STRONGEST_BASIC>
-4.154114281276843

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
144.12740000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.90e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bongkrek acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 72  0  0  0  0  0  0  0  0999 V2000
   -4.4099   -2.2890    2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8893   -1.1118    2.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.1925    1.5317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2452    1.0235    1.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5034    2.0268    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    2.4079   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231    1.8908   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185    2.3128   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    1.8206   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235    0.7908   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8635    0.4555   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657   -0.7114   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806   -1.0479   -0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    0.0817   -0.6681 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4321    1.1010   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1258   -0.4525   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320   -0.3010    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4114   -0.8333   -0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2668   -0.6722    0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0094   -0.0080    2.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9438    0.4973    2.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0496    0.0892    3.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7038   -1.5138   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0076   -2.0701   -1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2600   -2.4945   -2.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5479    0.3199    1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0130   -0.4450   -1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3403    0.1241   -1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4776   -1.5808   -3.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -1.9926    1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2169    0.6743    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8334    1.1536    0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2639    1.4248   -2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424    2.6810   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1808    1.0386    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1526   -0.1432   -0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469    1.2968   -0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503   -1.5442   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8771   -1.5657   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311   -1.8697   -0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    0.6267    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    0.8893   -2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2802    1.1328   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830    2.1138   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4123   -0.9579   -1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786    0.2000    0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3121   -1.0650    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1663    0.9965    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400   -0.7189   -2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9013   -2.2811   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3401   -3.1305   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0648    1.1308    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6067    0.3276    3.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041    1.9783    2.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4239    0.6343    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1355   -0.8222   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2234    1.2128   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8359   -0.3309   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9954    0.0752   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2675   -2.5603   -2.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  8  9  1  0
  9 10  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
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 18 23  1  0
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 24 25  2  0
 24 26  1  0
  3 27  1  0
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 27 29  2  0
 29 30  1  0
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 31 32  1  0
 31 33  1  0
 33 34  2  0
 33 35  1  0
  1 36  1  0
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  1 38  1  0
  3 39  1  6
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 32 72  1  0
 35 73  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.410  -2.289   2.001  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.889  -1.112   2.564  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.177  -0.193   1.532  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.245   1.024   1.712  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.503   2.027   0.664  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.580   2.408  -0.184  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.223   1.891  -0.183  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.319   2.313  -1.070  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.035   1.821  -1.096  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.424   0.791  -0.084  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.863   0.456  -0.282  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.366  -0.711  -0.568  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.781  -1.048  -0.767  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.743   0.082  -0.668  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.432   1.101  -1.746  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.126  -0.453  -0.835  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.032  -0.301   0.150  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.411  -0.833  -0.017  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.267  -0.672   0.946  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.009  -0.008   2.205  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.944   0.497   2.539  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.050   0.089   3.162  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.704  -1.514  -1.279  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.008  -2.070  -1.535  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.260  -2.494  -2.746  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.064  -2.235  -0.687  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.548   0.320   1.621  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.960   0.988   2.922  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.419   0.233   0.642  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.078  -0.386  -0.616  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.013  -0.445  -1.583  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.340   0.124  -1.316  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.746  -1.053  -2.877  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.614  -1.107  -3.771  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.478  -1.581  -3.094  0.00  0.00           O+0
HETATM   36  H   UNK     0      -3.482  -1.993   1.434  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.130  -2.978   2.822  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.123  -2.739   1.291  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.938  -0.682   0.595  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.217   0.674   1.794  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.550   1.482   2.697  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.519   2.450   0.623  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.818   3.149  -0.938  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.833   1.154   0.496  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.619   3.054  -1.796  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.264   1.425  -2.131  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.742   2.681  -0.974  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.181   1.039   0.943  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.153  -0.143  -0.336  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.547   1.297  -0.154  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.650  -1.544  -0.674  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.877  -1.566  -1.762  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.031  -1.870  -0.031  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.678   0.627   0.301  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.480   0.889  -2.279  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.280   1.133  -2.496  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.383   2.114  -1.340  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.412  -0.958  -1.736  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.679   0.200   0.989  0.00  0.00           H+0
HETATM   60  H   UNK     0      10.312  -1.065   0.824  0.00  0.00           H+0
HETATM   61  H   UNK     0      10.166   0.997   3.584  0.00  0.00           H+0
HETATM   62  H   UNK     0       8.540  -0.719  -2.083  0.00  0.00           H+0
HETATM   63  H   UNK     0       7.901  -2.281  -1.522  0.00  0.00           H+0
HETATM   64  H   UNK     0      11.340  -3.131  -0.311  0.00  0.00           H+0
HETATM   65  H   UNK     0      -8.065   1.131   2.943  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.607   0.328   3.724  0.00  0.00           H+0
HETATM   67  H   UNK     0      -6.504   1.978   2.989  0.00  0.00           H+0
HETATM   68  H   UNK     0      -8.424   0.634   0.772  0.00  0.00           H+0
HETATM   69  H   UNK     0      -6.136  -0.822  -0.888  0.00  0.00           H+0
HETATM   70  H   UNK     0      -9.223   1.213  -1.038  0.00  0.00           H+0
HETATM   71  H   UNK     0      -9.836  -0.331  -0.423  0.00  0.00           H+0
HETATM   72  H   UNK     0      -9.995   0.075  -2.195  0.00  0.00           H+0
HETATM   73  H   UNK     0      -6.268  -2.560  -2.934  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   27   39                                             
CONECT    4    3    5   40   41                                             
CONECT    5    4    6   42                                                  
CONECT    6    5    7   43                                                  
CONECT    7    6    8   44                                                  
CONECT    8    7    9   45                                                  
CONECT    9    8   10   46   47                                             
CONECT   10    9   11   48   49                                             
CONECT   11   10   12   50                                                  
CONECT   12   11   13   51                                                  
CONECT   13   12   14   52   53                                             
CONECT   14   13   15   16   54                                             
CONECT   15   14   55   56   57                                             
CONECT   16   14   17   58                                                  
CONECT   17   16   18   59                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   60                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   61                                                       
CONECT   23   18   24   62   63                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   64                                                       
CONECT   27    3   28   29                                                  
CONECT   28   27   65   66   67                                             
CONECT   29   27   30   68                                                  
CONECT   30   29   31   69                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   70   71   72                                             
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   73                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   15                                                            
CONECT   58   16                                                            
CONECT   59   17                                                            
CONECT   60   19                                                            
CONECT   61   22                                                            
CONECT   62   23                                                            
CONECT   63   23                                                            
CONECT   64   26                                                            
CONECT   65   28                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
CONECT   68   29                                                            
CONECT   69   30                                                            
CONECT   70   32                                                            
CONECT   71   32                                                            
CONECT   72   32                                                            
CONECT   73   35                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  144    0
END

RDKit          3D

73 72  0  0  0  0  0  0  0  0999 V2000
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   11.3401   -3.1305   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0648    1.1308    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6067    0.3276    3.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041    1.9783    2.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4239    0.6343    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1355   -0.8222   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2234    1.2128   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8359   -0.3309   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9954    0.0752   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2675   -2.5603   -2.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  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
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  3 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 33 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  6
  4 40  1  0
  4 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  1
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 17 59  1  0
 19 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 30 69  1  0
 32 70  1  0
 32 71  1  0
 32 72  1  0
 35 73  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Bongkrekic acid	ChEBI
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyl-2,4,8,10,14,18,20-docosaheptaenedioic acid	ChEBI
Bongkrek acid	ChEBI
(-)-Bongkrekate	Generator
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyl-2,4,8,10,14,18,20-docosaheptaenedioate	Generator
Bongkrekate	Generator
Flavotoxin a	MeSH

Chemical Formula

C₂₈H₃₈O₇

Average Mass

486.6050 Da

Monoisotopic Mass

486.26175 Da

IUPAC Name

(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid

Traditional Name

bongkrek acid

CAS Registry Number

Not Available

SMILES

CO[C@H](C\C=C/C=C/CC\C=C\C[C@H](C)\C=C\C(\CC(O)=O)=C/C(O)=O)C(\C)=C/C=C(\C)C(O)=O

InChI Identifier

InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1

InChI Key

SHCXABJSXUACKU-WUTQZGRKSA-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
Burkholderia gladioli	LOTUS Database	35616633
Pseudomonas	NPAtlas	1276139

Chemical Taxonomy

Classification

Not classified

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	5.04	ALOGPS
logP	5.5	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	144.13 m³·mol⁻¹	ChemAxon
Polarizability	55.96 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA017560

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4938689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bongkrek_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

77742

Good Scents ID

Not Available

References

General References

Lauquin GJ, Duplaa AM, Klein G, Rousseau A, Vignais PV: Isobongkrekic acid, a new inhibitor of mitochondrial ADP-ATP transport: radioactive labeling and chemical and biological properties. Biochemistry. 1976 Jun 1;15(11):2323-7. doi: 10.1021/bi00656a012. [PubMed:1276139 ]
de Graaf AO, Meijerink JP, van den Heuvel LP, DeAbreu RA, de Witte T, Jansen JH, Smeitink JA: Bcl-2 protects against apoptosis induced by antimycin A and bongkrekic acid without restoring cellular ATP levels. Biochim Biophys Acta. 2002 Apr 22;1554(1-2):57-65. doi: 10.1016/s0005-2728(02)00213-x. [PubMed:12034471 ]
Muranyi M, Li PA: Bongkrekic acid ameliorates ischemic neuronal death in the cortex by preventing cytochrome c release and inhibiting astrocyte activation. Neurosci Lett. 2005 Aug 26;384(3):277-81. doi: 10.1016/j.neulet.2005.05.011. [PubMed:15919152 ]
Malekova L, Kominkova V, Ferko M, Stefanik P, Krizanova O, Ziegelhoffer A, Szewczyk A, Ondrias K: Bongkrekic acid and atractyloside inhibits chloride channels from mitochondrial membranes of rat heart. Biochim Biophys Acta. 2007 Jan;1767(1):31-44. doi: 10.1016/j.bbabio.2006.10.004. Epub 2006 Oct 14. [PubMed:17123460 ]
Rohm B, Scherlach K, Hertweck C: Biosynthesis of the mitochondrial adenine nucleotide translocase (ATPase) inhibitor bongkrekic acid in Burkholderia gladioli. Org Biomol Chem. 2010 Apr 7;8(7):1520-2. doi: 10.1039/b925483h. Epub 2010 Feb 5. [PubMed:20237660 ]

Showing NP-Card for Isobongkrekic acid, (NP0004618)

MOL for NP0004618 (Isobongkrekic acid,)

3D MOL for NP0004618 (Isobongkrekic acid,)

3D SDF for NP0004618 (Isobongkrekic acid,)

3D-SDF for NP0004618 (Isobongkrekic acid,)

PDB for NP0004618 (Isobongkrekic acid,)

3D PDB for NP0004618 (Isobongkrekic acid,)

SMILES for NP0004618 (Isobongkrekic acid,)

INCHI for NP0004618 (Isobongkrekic acid,)

Structure for NP0004618 (Isobongkrekic acid,)

3D Structure for NP0004618 (Isobongkrekic acid,)