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Showing NP-Card for gambieric acid c (NP0259470)

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Record Information
Version2.0
Created at2022-09-08 01:21:19 UTC
Updated at2022-09-08 01:21:19 UTC
NP-MRD IDNP0259470
Secondary Accession NumbersNone
Natural Product Identification
Common Namegambieric acid c
Description(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]Tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. gambieric acid c is found in Gambierdiscus toxicus. These are carboxylic acids containing exactly three carboxyl groups (3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]Tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]Tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0259470 (gambieric acid c)


  Mrv0541 09111411562D          

111120  0  0  1  0            999 V2000
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   11.0156    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
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3D MOL for NP0259470 (gambieric acid c)

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3D SDF for NP0259470 (gambieric acid c)

  Mrv0541 09111411562D          

111120  0  0  1  0            999 V2000
    4.5416   -3.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9107    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4232   -2.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0156    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2661   -1.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3688   -3.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2274   -2.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6655    0.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9367   -1.9660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6614    1.3143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   21.5028   -2.7231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.5479   -1.8959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2357   -0.4646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7492    0.1811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8766   -1.0940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3845   -2.3314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0345   -2.5416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6942   -1.8985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7022   -0.2357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0434   -1.2835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0259470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=C(C)C[C@]1([H])O[C@]2(C)C[C@]3([H])O[C@]4([H])C[C@]5([H])O[C@]6([H])CC[C@]7([H])O[C@]8([H])C[C@]9([H])O[C@]([H])(C[C@]([H])(O)C[C@]%10([H])C[C@@]([H])(C)[C@]([H])(O%10)[C@@]([H])(C)CC(O)=O)[C@@]([H])(O)CC[C@@]9([H])O[C@@]8(C)C[C@@]7(C)O[C@@]6([H])C\C([H])=C([H])/[C@@]([H])(C)[C@@]5([H])O[C@@]4(C)[C@]([H])(O)[C@@]3([H])O[C@@]2([H])CC1=C)[C@@]([H])(C)COC(=O)C[C@@]([H])(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C65H100O19/c1-33(19-35(3)31-74-57(72)22-34(2)21-55(68)69)20-46-37(5)24-52-62(8,83-46)30-50-60(80-52)61(73)65(11)54(78-50)29-49-59(84-65)36(4)13-12-14-44-43(76-49)17-18-51-63(9,81-44)32-64(10)53(79-51)28-48-45(82-64)16-15-42(67)47(77-48)27-40(66)26-41-23-38(6)58(75-41)39(7)25-56(70)71/h12-13,19,34-36,38-54,58-61,66-67,73H,5,14-18,20-32H2,1-4,6-11H3,(H,68,69)(H,70,71)/b13-12-,33-19+/t34-,35+,36+,38+,39-,40+,41-,42-,43+,44-,45+,46-,47+,48-,49-,50-,51-,52-,53+,54+,58-,59+,60-,61+,62+,63+,64-,65+/m0/s1

> <INCHI_KEY>
PAZSGUQEBJPONR-NMYRWGSKSA-N

> <FORMULA>
C65H100O19

> <MOLECULAR_WEIGHT>
1185.4781

> <EXACT_MASS>
1184.685881018

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
184

> <JCHEM_AVERAGE_POLARIZABILITY>
133.88115853688316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
5.400952393333331

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.813539018316015

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2069550388471635

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7601361315436606

> <JCHEM_POLAR_SURFACE_AREA>
253.8899999999999

> <JCHEM_REFRACTIVITY>
306.8140999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0259470 (gambieric acid c)
Download
PDB for NP0259470 (gambieric acid c)
HEADER    PROTEIN                                 11-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-14         0                                  
HETATM    1  C   UNK     0       8.478  -6.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.567   2.289   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.390  -4.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.563   3.412   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.830  -2.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.622  -7.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      45.225  -4.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.964  -4.807   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.619   0.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.109   0.050   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.233   1.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.604   3.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.081   3.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.625   1.878   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.145  -2.038   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.756  -1.372   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.052  -2.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.440  -3.034   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.872  -3.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.959  -5.557   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.085   1.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.173  -0.350   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      40.950  -6.392   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.312  -1.714   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      43.819  -2.138   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.603  -4.970   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.201  -6.131   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.558  -4.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.886  -1.645   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.923  -3.601   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.784  -2.237   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.638  -0.406   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.436  -5.330   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.608   1.083   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.348  -3.670   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.768   2.453   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.353  -2.919   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      42.446  -6.025   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      43.867  -3.678   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      37.737  -6.244   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      40.139  -5.083   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      36.489  -3.539   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.707  -0.867   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      25.665   0.338   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      33.370  -2.042   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.918  -4.352   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      35.531  -4.744   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      33.029  -3.544   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      21.844  -0.440   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      16.881  -2.396   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      27.826  -2.364   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.835  -1.941   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      30.428  -2.954   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      19.363  -1.418   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.520   2.743   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      45.128  -1.327   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.696  -0.577   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      42.558  -4.489   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      21.280   0.993   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      16.316  -0.963   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      17.275   0.242   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      14.399  -3.374   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      28.167  -0.862   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      30.768  -1.452   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      18.798   0.015   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      38.407  -7.630   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      37.991  -3.880   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      -1.003   2.971   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0       1.479   3.949   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      46.485  -2.055   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      45.080   0.212   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       5.654   0.628   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      16.710   1.675   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0       5.261  -2.010   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      41.133  -3.907   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      23.198  -1.175   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      33.991  -4.747   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      18.404  -2.623   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      28.957  -3.410   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      14.793  -0.736   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      27.205   0.340   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0      32.239  -0.996   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0      13.441  -4.579   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      19.756   1.220   0.000  0.00  0.00           O+0
HETATM   85  H   UNK     0      25.339   4.384   0.000  0.00  0.00           H+0
HETATM   86  H   UNK     0      22.774   4.767   0.000  0.00  0.00           H+0
HETATM   87  H   UNK     0       8.307  -2.464   0.000  0.00  0.00           H+0
HETATM   88  H   UNK     0       2.044   2.516   0.000  0.00  0.00           H+0
HETATM   89  H   UNK     0       7.913  -5.103   0.000  0.00  0.00           H+0
HETATM   90  H   UNK     0      22.973   1.495   0.000  0.00  0.00           H+0
HETATM   91  H   UNK     0      43.865  -5.428   0.000  0.00  0.00           H+0
HETATM   92  H   UNK     0      45.176  -2.866   0.000  0.00  0.00           H+0
HETATM   93  H   UNK     0      37.067  -4.857   0.000  0.00  0.00           H+0
HETATM   94  H   UNK     0      39.542  -3.663   0.000  0.00  0.00           H+0
HETATM   95  H   UNK     0      34.988  -3.198   0.000  0.00  0.00           H+0
HETATM   96  H   UNK     0      23.902   0.446   0.000  0.00  0.00           H+0
HETATM   97  H   UNK     0      26.335  -1.048   0.000  0.00  0.00           H+0
HETATM   98  H   UNK     0      34.575  -3.001   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0      10.395  -4.125   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0      34.714  -6.050   0.000  0.00  0.00           H+0
HETATM  101  H   UNK     0      31.899  -2.498   0.000  0.00  0.00           H+0
HETATM  102  H   UNK     0      22.997   0.581   0.000  0.00  0.00           H+0
HETATM  103  H   UNK     0      17.839  -1.191   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      26.621  -1.406   0.000  0.00  0.00           H+0
HETATM  105  H   UNK     0      15.358  -2.169   0.000  0.00  0.00           H+0
HETATM  106  H   UNK     0      29.297  -1.908   0.000  0.00  0.00           H+0
HETATM  107  H   UNK     0      19.927  -2.851   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0      42.430  -2.954   0.000  0.00  0.00           H+0
HETATM  109  H   UNK     0      20.321  -0.213   0.000  0.00  0.00           H+0
HETATM  110  H   UNK     0      15.752   0.470   0.000  0.00  0.00           H+0
HETATM  111  H   UNK     0      16.069   1.201   0.000  0.00  0.00           H+0
CONECT    1   33                                                            
CONECT    2   34                                                            
CONECT    3   35                                                            
CONECT    4   36                                                            
CONECT    5   37                                                            
CONECT    6   38                                                            
CONECT    7   39                                                            
CONECT    8   62                                                            
CONECT    9   63                                                            
CONECT   10   64                                                            
CONECT   11   65                                                            
CONECT   12   13   14   85                                                  
CONECT   13   12   36   86                                                  
CONECT   14   12   44                                                       
CONECT   15   16   42                                                       
CONECT   16   15   45                                                       
CONECT   17   18   43                                                       
CONECT   18   17   51                                                       
CONECT   19   33   35   87                                                  
CONECT   20   33   46                                                       
CONECT   21   34   55                                                       
CONECT   22   34   57                                                       
CONECT   23   38   41                                                       
CONECT   24   37   52                                                       
CONECT   25   39   56                                                       
CONECT   26   40   41                                                       
CONECT   27   40   47                                                       
CONECT   28   48   53                                                       
CONECT   29   49   54                                                       
CONECT   30   50   62                                                       
CONECT   31   35   74                                                       
CONECT   32   63   64                                                       
CONECT   33    1   19   20                                                  
CONECT   34    2   21   22   88                                             
CONECT   35    3   19   31   89                                             
CONECT   36    4   13   59   90                                             
CONECT   37    5   24   46                                                  
CONECT   38    6   23   58   91                                             
CONECT   39    7   25   58   92                                             
CONECT   40   26   27   66   93                                             
CONECT   41   23   26   75   94                                             
CONECT   42   15   47   67   95                                             
CONECT   43   17   44   76   96                                             
CONECT   44   14   43   81   97                                             
CONECT   45   16   48   82   98                                             
CONECT   46   20   37   83   99                                             
CONECT   47   27   42   77  100                                             
CONECT   48   28   45   77  101                                             
CONECT   49   29   59   76  102                                             
CONECT   50   30   60   78  103                                             
CONECT   51   18   63   79  104                                             
CONECT   52   24   62   80  105                                             
CONECT   53   28   64   79  106                                             
CONECT   54   29   65   78  107                                             
CONECT   55   21   68   69                                                  
CONECT   56   25   70   71                                                  
CONECT   57   22   72   74                                                  
CONECT   58   38   39   75  108                                             
CONECT   59   36   49   84  109                                             
CONECT   60   50   61   80  110                                             
CONECT   61   60   65   73  111                                             
CONECT   62    8   30   52   83                                             
CONECT   63    9   32   51   81                                             
CONECT   64   10   32   53   82                                             
CONECT   65   11   54   61   84                                             
CONECT   66   40                                                            
CONECT   67   42                                                            
CONECT   68   55                                                            
CONECT   69   55                                                            
CONECT   70   56                                                            
CONECT   71   56                                                            
CONECT   72   57                                                            
CONECT   73   61                                                            
CONECT   74   31   57                                                       
CONECT   75   41   58                                                       
CONECT   76   43   49                                                       
CONECT   77   47   48                                                       
CONECT   78   50   54                                                       
CONECT   79   51   53                                                       
CONECT   80   52   60                                                       
CONECT   81   44   63                                                       
CONECT   82   45   64                                                       
CONECT   83   46   62                                                       
CONECT   84   59   65                                                       
CONECT   85   12                                                            
CONECT   86   13                                                            
CONECT   87   19                                                            
CONECT   88   34                                                            
CONECT   89   35                                                            
CONECT   90   36                                                            
CONECT   91   38                                                            
CONECT   92   39                                                            
CONECT   93   40                                                            
CONECT   94   41                                                            
CONECT   95   42                                                            
CONECT   96   43                                                            
CONECT   97   44                                                            
CONECT   98   45                                                            
CONECT   99   46                                                            
CONECT  100   47                                                            
CONECT  101   48                                                            
CONECT  102   49                                                            
CONECT  103   50                                                            
CONECT  104   51                                                            
CONECT  105   52                                                            
CONECT  106   53                                                            
CONECT  107   54                                                            
CONECT  108   58                                                            
CONECT  109   59                                                            
CONECT  110   60                                                            
CONECT  111   61                                                            
MASTER        0    0    0    0    0    0    0    0  111    0  240    0
END

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3D PDB for NP0259470 (gambieric acid c)
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SMILES for NP0259470 (gambieric acid c)
[H]C(=C(C)C[C@]1([H])O[C@]2(C)C[C@]3([H])O[C@]4([H])C[C@]5([H])O[C@]6([H])CC[C@]7([H])O[C@]8([H])C[C@]9([H])O[C@]([H])(C[C@]([H])(O)C[C@]%10([H])C[C@@]([H])(C)[C@]([H])(O%10)[C@@]([H])(C)CC(O)=O)[C@@]([H])(O)CC[C@@]9([H])O[C@@]8(C)C[C@@]7(C)O[C@@]6([H])C\C([H])=C([H])/[C@@]([H])(C)[C@@]5([H])O[C@@]4(C)[C@]([H])(O)[C@@]3([H])O[C@@]2([H])CC1=C)[C@@]([H])(C)COC(=O)C[C@@]([H])(C)CC(O)=O
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INCHI for NP0259470 (gambieric acid c)
InChI=1S/C65H100O19/c1-33(19-35(3)31-74-57(72)22-34(2)21-55(68)69)20-46-37(5)24-52-62(8,83-46)30-50-60(80-52)61(73)65(11)54(78-50)29-49-59(84-65)36(4)13-12-14-44-43(76-49)17-18-51-63(9,81-44)32-64(10)53(79-51)28-48-45(82-64)16-15-42(67)47(77-48)27-40(66)26-41-23-38(6)58(75-41)39(7)25-56(70)71/h12-13,19,34-36,38-54,58-61,66-67,73H,5,14-18,20-32H2,1-4,6-11H3,(H,68,69)(H,70,71)/b13-12-,33-19+/t34-,35+,36+,38+,39-,40+,41-,42-,43+,44-,45+,46-,47+,48-,49-,50-,51-,52-,53+,54+,58-,59+,60-,61+,62+,63+,64-,65+/m0/s1
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View in JSmol
Synonyms
ValueSource
(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0,.0,.0,.0,.0,.0,.0,]tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoateGenerator
(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoateGenerator
Gambierate CGenerator
Chemical FormulaC65H100O19
Average Mass1185.4781 Da
Monoisotopic Mass1184.68588 Da
IUPAC Name(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid
Traditional Name(3S)-5-{[(2R)-5-[(1R,3S,5R,7S,9R,11S,14S,16R,17R,18S,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-35-[(2R)-3-[(2S,4R,5S)-5-[(2S)-1-carboxypropan-2-yl]-4-methyloxolan-2-yl]-2-hydroxypropyl]-17,34-dihydroxy-9,18,21,27,29-pentamethyl-12-methylidene-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.0³,²⁰.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴¹.0²⁹,³⁹.0³¹,³⁷]tritetracont-22-en-11-yl]-2,4-dimethylpent-3-en-1-yl]oxy}-3-methyl-5-oxopentanoic acid
CAS Registry NumberNot Available
SMILES
[H]C(=C(C)C[C@]1([H])O[C@]2(C)C[C@]3([H])O[C@]4([H])C[C@]5([H])O[C@]6([H])CC[C@]7([H])O[C@]8([H])C[C@]9([H])O[C@]([H])(C[C@]([H])(O)C[C@]%10([H])C[C@@]([H])(C)[C@]([H])(O%10)[C@@]([H])(C)CC(O)=O)[C@@]([H])(O)CC[C@@]9([H])O[C@@]8(C)C[C@@]7(C)O[C@@]6([H])C\C([H])=C([H])/[C@@]([H])(C)[C@@]5([H])O[C@@]4(C)[C@]([H])(O)[C@@]3([H])O[C@@]2([H])CC1=C)[C@@]([H])(C)COC(=O)C[C@@]([H])(C)CC(O)=O
InChI Identifier
InChI=1S/C65H100O19/c1-33(19-35(3)31-74-57(72)22-34(2)21-55(68)69)20-46-37(5)24-52-62(8,83-46)30-50-60(80-52)61(73)65(11)54(78-50)29-49-59(84-65)36(4)13-12-14-44-43(76-49)17-18-51-63(9,81-44)32-64(10)53(79-51)28-48-45(82-64)16-15-42(67)47(77-48)27-40(66)26-41-23-38(6)58(75-41)39(7)25-56(70)71/h12-13,19,34-36,38-54,58-61,66-67,73H,5,14-18,20-32H2,1-4,6-11H3,(H,68,69)(H,70,71)/b13-12-,33-19+/t34-,35+,36+,38+,39-,40+,41-,42-,43+,44-,45+,46-,47+,48-,49-,50-,51-,52-,53+,54+,58-,59+,60-,61+,62+,63+,64-,65+/m0/s1
InChI KeyPAZSGUQEBJPONR-NMYRWGSKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gambierdiscus toxicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassTricarboxylic acids and derivatives  
Direct ParentTricarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
    • 

  • Fatty acid ester
    • 

  • Oxepane
    • 

  • Monosaccharide
    • 

  • Oxane
    • 

  • Fatty acyl
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.94ALOGPS
logP5.4ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area253.89 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity306.81 m³·mol⁻¹ChemAxon
Polarizability133.88 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16887  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46173844  
PDB IDNot Available
ChEBI ID80779  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]