NP-MRD: Showing NP-Card for GR 105155X (NP0061520)

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Record Information

Version

2.0

Created at

2022-04-28 06:17:58 UTC

Updated at

2022-04-28 06:17:58 UTC

NP-MRD ID

NP0061520

Secondary Accession Numbers

None

Natural Product Identification

Common Name

GR 105155X

Description

Zaragozic acid A, also known as squalestatin 1 or zaragozate a, belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. GR 105155X is found in Exserohilum khartoumense and Sporormiella intermedia. GR 105155X was first documented in 1992 (PMID: 1601846). Zaragozic acid A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 10987953) (PMID: 12391282) (PMID: 20722739) (PMID: 21183681).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041413482D          

 58 60  0  0  1  0            999 V2000
   -3.3373   -3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -4.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -4.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884    1.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -3.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481    1.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4625    1.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4510    2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798    0.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    1.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -3.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -0.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -3.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4999    0.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9372   -3.6667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5371   -3.9523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3230    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    0.3963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7518   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    0.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -0.1877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086   -0.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8427    0.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9662   -2.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -3.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -2.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -2.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -2.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019   -1.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    0.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341    0.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345   -0.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8631   -4.2378    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -2.3356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -3.9282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2855    0.9803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057    0.6089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2118   -1.9426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -1.0800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 14 13  2  0  0  0  0
 16 15  1  0  0  0  0
 19  2  1  1  0  0  0
 19  7  1  0  0  0  0
 19 17  1  0  0  0  0
 20  3  1  1  0  0  0
 20 13  1  0  0  0  0
 20 17  1  0  0  0  0
 21  4  2  0  0  0  0
 21 15  1  0  0  0  0
 22  5  1  1  0  0  0
 22 18  1  0  0  0  0
 23  6  1  0  0  0  0
 24 11  2  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29 30  1  1  0  0  0
 33 16  1  1  0  0  0
 33 27  1  0  0  0  0
 34 29  1  0  0  0  0
 34 31  1  6  0  0  0
 35 28  1  0  0  0  0
 35 32  1  6  0  0  0
 35 34  1  0  0  0  0
 36 23  2  0  0  0  0
 37 25  2  0  0  0  0
 27 38  1  1  0  0  0
 39 30  2  0  0  0  0
 40 30  1  0  0  0  0
 41 31  2  0  0  0  0
 42 31  1  0  0  0  0
 43 32  2  0  0  0  0
 44 32  1  0  0  0  0
 34 45  1  1  0  0  0
 46 23  1  0  0  0  0
 26 46  1  6  0  0  0
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 22 54  1  6  0  0  0
 26 55  1  6  0  0  0
 27 56  1  6  0  0  0
 28 57  1  1  0  0  0
 29 58  1  6  0  0  0
M  END

     RDKit          3D

 95 97  0  0  0  0  0  0  0  0999 V2000
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   -3.8314   -1.3694    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -0.8573   -0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -0.9326   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -0.0850    0.6543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1371    0.0817    1.9194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348    1.3521    2.4388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1539    2.2840    1.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472    3.4291    2.4822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164    2.0613    0.8809 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948    2.0586    2.1568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0326    3.4601    2.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1277    1.7609    3.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3835    0.6203    3.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392    2.8031    3.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043    1.7057    0.7620 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1452    2.8924    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914    3.2645   -1.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    3.5494    0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037    1.2143    0.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    0.5807    0.7616 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4469    0.7578   -0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249    0.7457   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2813    0.3664    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2343   -1.1489   -1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6079   -1.4757   -2.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8741    0.6488   -3.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0645    1.9133   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5  4  1  6
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 36  1  0
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  8 10  1  0
  8  9  2  0
 16 21  1  0
  6  5  1  0
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  1 50  1  0
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 48 94  1  0
 49 95  1  0
 19 60  1  0
 12 58  1  0
 15 59  1  0
  7 56  1  1
 10 57  1  0
M  END


  Mrv0541 05041413482D          

 58 60  0  0  1  0            999 V2000
   -3.3373   -3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -4.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -4.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884    1.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -3.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481    1.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4625    1.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4510    2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798    0.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    1.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -3.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -0.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -3.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4999    0.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9372   -3.6667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5371   -3.9523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3230    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    0.3963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7518   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    0.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -0.1877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086   -0.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8427    0.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9662   -2.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -3.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -2.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -2.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -2.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019   -1.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    0.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341    0.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345   -0.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8631   -4.2378    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -2.3356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197   -3.9282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806   -4.4992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855    0.9803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057    0.6089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0755   -2.4665    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118   -1.9426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -1.0800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 14 13  2  0  0  0  0
 16 15  1  0  0  0  0
 19  2  1  1  0  0  0
 19  7  1  0  0  0  0
 19 17  1  0  0  0  0
 20  3  1  1  0  0  0
 20 13  1  0  0  0  0
 20 17  1  0  0  0  0
 21  4  2  0  0  0  0
 21 15  1  0  0  0  0
 22  5  1  1  0  0  0
 22 18  1  0  0  0  0
 23  6  1  0  0  0  0
 24 11  2  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29 30  1  1  0  0  0
 33 16  1  1  0  0  0
 33 27  1  0  0  0  0
 34 29  1  0  0  0  0
 34 31  1  6  0  0  0
 35 28  1  0  0  0  0
 35 32  1  6  0  0  0
 35 34  1  0  0  0  0
 36 23  2  0  0  0  0
 37 25  2  0  0  0  0
 27 38  1  1  0  0  0
 39 30  2  0  0  0  0
 40 30  1  0  0  0  0
 41 31  2  0  0  0  0
 42 31  1  0  0  0  0
 43 32  2  0  0  0  0
 44 32  1  0  0  0  0
 34 45  1  1  0  0  0
 46 23  1  0  0  0  0
 26 46  1  6  0  0  0
 47 25  1  0  0  0  0
 28 47  1  6  0  0  0
 48 29  1  0  0  0  0
 48 33  1  0  0  0  0
 49 33  1  0  0  0  0
 49 35  1  0  0  0  0
 50 13  1  0  0  0  0
 51 14  1  0  0  0  0
 19 52  1  6  0  0  0
 20 53  1  6  0  0  0
 22 54  1  6  0  0  0
 26 55  1  6  0  0  0
 27 56  1  6  0  0  0
 28 57  1  1  0  0  0
 29 58  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0061520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])[C@@]([H])(C)C[C@@]([H])(C)CC)C(=O)O[C@]1([H])[C@@]([H])(O)[C@]2(CCC(=C)[C@@]([H])(OC(C)=O)[C@]([H])(C)CC3=CC=CC=C3)O[C@@]1(C(O)=O)[C@](O)(C(O)=O)[C@]([H])(O2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1

> <INCHI_KEY>
DFKDOZMCHOGOBR-NCSQYGPNSA-N

> <FORMULA>
C35H46O14

> <MOLECULAR_WEIGHT>
690.7313

> <EXACT_MASS>
690.28875618

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
71.24109294305333

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
5.257308069333331

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.275255117094465

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3979464166333937

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0341077274906505

> <JCHEM_POLAR_SURFACE_AREA>
223.41999999999993

> <JCHEM_REFRACTIVITY>
169.5212000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zaragozic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6   23                                                            
CONECT    7    1   19                                                       
CONECT    8    9   10                                                       
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   24                                                       
CONECT   12   10   24                                                       
CONECT   13   14   20   50                                                  
CONECT   14   13   25   51                                                  
CONECT   15   16   21                                                       
CONECT   16   15   33                                                       
CONECT   17   19   20                                                       
CONECT   18   22   24                                                       
CONECT   19    2    7   17   52                                             
CONECT   20    3   13   17   53                                             
CONECT   21    4   15   26                                                  
CONECT   22    5   18   26   54                                             
CONECT   23    6   36   46                                                  
CONECT   24   11   12   18                                                  
CONECT   25   14   37   47                                                  
CONECT   26   21   22   46   55                                             
CONECT   27   28   33   38   56                                             
CONECT   28   27   35   47   57                                             
CONECT   29   30   34   48   58                                             
CONECT   30   29   39   40                                                  
CONECT   31   34   41   42                                                  
CONECT   32   35   43   44                                                  
CONECT   33   16   27   48   49                                             
CONECT   34   29   31   35   45                                             
CONECT   35   28   32   34   49                                             
CONECT   36   23                                                            
CONECT   37   25                                                            
CONECT   38   27                                                            
CONECT   39   30                                                            
CONECT   40   30                                                            
CONECT   41   31                                                            
CONECT   42   31                                                            
CONECT   43   32                                                            
CONECT   44   32                                                            
CONECT   45   34                                                            
CONECT   46   23   26                                                       
CONECT   47   25   28                                                       
CONECT   48   29   33                                                       
CONECT   49   33   35                                                       
CONECT   50   13                                                            
CONECT   51   14                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   22                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

View in JSmol

Synonyms

Value	Source
1S-((4S-Acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(e)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylic acid	ChEBI
Squalestatin 1	ChEBI
1S-((4S-Acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(e)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylate	Generator
Zaragozate a	Generator
Squalestatin	MeSH
7-Deoxy zaragozic acid	MeSH
Squalestatin S1	MeSH

Chemical Formula

C₃₅H₄₆O₁₄

Average Mass

690.7313 Da

Monoisotopic Mass

690.28876 Da

IUPAC Name

(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

Traditional Name

zaragozic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@@]([H])(C)C[C@@]([H])(C)CC)C(=O)O[C@]1([H])[C@@]([H])(O)[C@]2(CCC(=C)[C@@]([H])(OC(C)=O)[C@]([H])(C)CC3=CC=CC=C3)O[C@@]1(C(O)=O)[C@](O)(C(O)=O)[C@]([H])(O2)C(O)=O

InChI Identifier

InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1

InChI Key

DFKDOZMCHOGOBR-NCSQYGPNSA-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
Exserohilum khartoumense	LOTUS Database	35616633
Sporormiella intermedia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Phenylpropane
Fatty acid ester
Ketal
Oxepane
Meta-dioxane
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Monosaccharide
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Acetal
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:75170 )
acetate ester (CHEBI:75170 )
tricarboxylic acid (CHEBI:75170 )
polyketide (CHEBI:75170 )
oxabicycloalkane (CHEBI:75170 )
cyclic ketal (CHEBI:75170 )
Other Polyketides (LMPK00000001 )

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	3.14	ALOGPS
logP	5.26	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	223.42 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	169.52 m³·mol⁻¹	ChemAxon
Polarizability	71.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zaragozic_acid

METLIN ID

Not Available

PubChem Compound

6438355

PDB ID

Not Available

ChEBI ID

75170

Good Scents ID

Not Available

References

General References

Freeman-Cook KD, Halcomb RL: A symmetry-based formal synthesis of zaragozic acid A. J Org Chem. 2000 Sep 22;65(19):6153-9. doi: 10.1021/jo000665j. [PubMed:10987953 ]
Kocarek TA, Mercer-Haines NA: Squalestatin 1-inducible expression of rat CYP2B: evidence that an endogenous isoprenoid is an activator of the constitutive androstane receptor. Mol Pharmacol. 2002 Nov;62(5):1177-86. doi: 10.1124/mol.62.5.1177. [PubMed:12391282 ]
Baxter A, Fitzgerald BJ, Hutson JL, McCarthy AD, Motteram JM, Ross BC, Sapra M, Snowden MA, Watson NS, Williams RJ, et al.: Squalestatin 1, a potent inhibitor of squalene synthase, which lowers serum cholesterol in vivo. J Biol Chem. 1992 Jun 15;267(17):11705-8. [PubMed:1601846 ]
Bhargava P, Kumar K, Chaudhaery SS, Saxena AK, Roy U: Cloning, overexpression and characterization of Leishmania donovani squalene synthase. FEMS Microbiol Lett. 2010 Oct;311(1):82-92. doi: 10.1111/j.1574-6968.2010.02071.x. Epub 2010 Aug 16. [PubMed:20722739 ]
Haeuptle MA, Welti M, Troxler H, Hulsmeier AJ, Imbach T, Hennet T: Improvement of dolichol-linked oligosaccharide biosynthesis by the squalene synthase inhibitor zaragozic acid. J Biol Chem. 2011 Feb 25;286(8):6085-91. doi: 10.1074/jbc.M110.165795. Epub 2010 Dec 23. [PubMed:21183681 ]

Showing NP-Card for GR 105155X (NP0061520)

MOL for NP0061520 (GR 105155X)

3D MOL for NP0061520 (GR 105155X)

3D SDF for NP0061520 (GR 105155X)

3D-SDF for NP0061520 (GR 105155X)

PDB for NP0061520 (GR 105155X)

3D PDB for NP0061520 (GR 105155X)

SMILES for NP0061520 (GR 105155X)

INCHI for NP0061520 (GR 105155X)

Structure for NP0061520 (GR 105155X)

3D Structure for NP0061520 (GR 105155X)