NP-MRD: Showing NP-Card for n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid (NP0314432)

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Record Information

Version

2.0

Created at

2022-09-11 12:31:35 UTC

Updated at

2022-09-11 12:31:35 UTC

NP-MRD ID

NP0314432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid

Description

N-[5-benzyl-8-(butan-2-yl)-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]Docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. N-[5-benzyl-8-(butan-2-yl)-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]Docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521202D          

 72 75  0  0  0  0            999 V2000
    9.1103   -8.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2855   -8.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8886   -9.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3165  -10.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6468  -10.3395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8183  -11.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5720  -11.4820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1038  -11.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0176  -12.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6850  -12.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4387  -12.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1061  -13.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0199  -13.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2662  -14.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988  -13.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4907  -11.0069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031  -10.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888  -10.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572  -11.7899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763  -10.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638  -10.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763  -11.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437  -12.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638  -12.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513  -10.2533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388  -10.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513  -11.6822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138  -10.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013  -10.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013   -8.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013   -7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5263   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -6.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3513   -7.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -6.5749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -6.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9214   -6.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.1086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -5.9664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -8.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -9.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 47 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
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 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
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 59 65  1  0  0  0  0
 43 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
  5 69  1  0  0  0  0
 69 70  2  0  0  0  0
 31 71  1  0  0  0  0
 26 71  1  0  0  0  0
 71 72  2  0  0  0  0
M  END

     RDKit          3D

146149  0  0  0  0  0  0  0  0999 V2000
   -0.1189    5.0093    2.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2139    3.7676    1.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    4.1308    0.5232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2758    5.2664   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727    2.9984   -0.4534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9047    1.9329    0.1879 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    1.2036   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919    0.0252   -0.7321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4519    1.5683   -0.2775 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6975    3.0173   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0938    3.4489   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8396    3.4263   -1.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1431    3.8544   -1.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7795    4.3293   -0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0693    4.3612    0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7397    3.9230    0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9946    1.0454    0.9743 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6387    1.7706    2.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052   -0.1159    1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8257   -0.0407    1.8126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5413   -1.4178    0.3973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8920   -2.1346    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8289   -1.2941   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1237   -2.0887   -0.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3497   -1.1001   -2.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7072   -2.2930    1.1732 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6764   -3.1680    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6695   -4.2523    0.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1775   -4.5390   -3.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8477   -1.4886   -1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171   -1.0699   -2.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6315   -0.6992   -0.3224 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7506    0.0039   -0.9185 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9155    0.3777   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714    0.1228    1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0211    1.1009   -0.8789 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6913    0.1771   -1.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103    0.8724   -2.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499    2.0540   -3.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234    2.9694   -3.9060 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9946    0.3821    1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1563   -2.1280    0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7382   -3.3777    0.7190 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8610    1.5057   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622    2.5231   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578    3.1927   -1.8951 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161521202D          

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 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 47 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 64 65  2  0  0  0  0
 59 65  1  0  0  0  0
 43 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
  5 69  1  0  0  0  0
 69 70  2  0  0  0  0
 31 71  1  0  0  0  0
 26 71  1  0  0  0  0
 71 72  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0314432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1NC(=O)C(CC2=CC=CC=C2)N(C)C(=O)C(CC(C)C)N2C(O)CCC(NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(O)CC3=CC=C(O)C=C3)C(C)OC1=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C51H74N8O13/c1-9-29(6)42-51(71)72-30(7)43(57-44(64)34(19-21-40(52)62)53-47(67)39(61)26-32-15-17-33(60)18-16-32)48(68)55-36(23-27(2)3)45(65)54-35-20-22-41(63)59(49(35)69)38(24-28(4)5)50(70)58(8)37(46(66)56-42)25-31-13-11-10-12-14-31/h10-18,27-30,34-39,41-43,60-61,63H,9,19-26H2,1-8H3,(H2,52,62)(H,53,67)(H,54,65)(H,55,68)(H,56,66)(H,57,64)

> <INCHI_KEY>
LWLFZSOQVBERAE-UHFFFAOYSA-N

> <FORMULA>
C51H74N8O13

> <MOLECULAR_WEIGHT>
1007.196

> <EXACT_MASS>
1006.537534475

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
146

> <JCHEM_AVERAGE_POLARIZABILITY>
104.9743313598205

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[5-benzyl-8-(butan-2-yl)-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-[2-hydroxy-3-(4-hydroxyphenyl)propanamido]pentanediamide

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.3993682129999987

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.415031167007616

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.496976843820088

> <JCHEM_PKA_STRONGEST_BASIC>
-3.462258440595046

> <JCHEM_POLAR_SURFACE_AREA>
316.2

> <JCHEM_REFRACTIVITY>
260.8933000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[5-benzyl-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-[2-hydroxy-3-(4-hydroxyphenyl)propanamido]pentanediamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      17.006 -16.389   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.466 -16.422   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.725 -17.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.524 -19.089   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.186 -17.806   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      12.407 -19.300   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.728 -20.807   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.134 -21.433   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.394 -21.577   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.233 -23.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.479 -24.014   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.886 -23.387   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.131 -24.292   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.970 -25.824   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.564 -26.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.318 -25.545   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      10.249 -20.546   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      10.832 -19.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.566 -20.473   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.693 -22.008   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.796 -19.139   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.026 -20.473   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.796 -21.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.042 -22.712   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.026 -23.140   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.256 -19.139   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       5.486 -20.473   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.256 -21.807   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.946 -20.473   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.176 -19.139   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.946 -17.806   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.176 -16.472   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       3.946 -15.138   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.176 -13.805   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.486 -15.138   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.716 -13.805   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.486 -12.471   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.716 -11.137   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.026 -12.471   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0       6.256 -13.805   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0       7.796 -13.805   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.635 -12.273   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       8.566 -15.138   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       9.336 -13.805   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0       8.566 -12.471   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       7.320 -11.566   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       9.336 -11.137   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.566  -9.804   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.566  -7.136   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       7.026  -7.136   0.000  0.00  0.00           O+0
HETATM   52  N   UNK     0       9.336  -5.803   0.000  0.00  0.00           N+0
HETATM   53  N   UNK     0      10.876 -11.137   0.000  0.00  0.00           N+0
HETATM   54  C   UNK     0      11.646  -9.804   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      10.876  -8.470   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      13.186  -9.804   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      13.956 -11.137   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      13.956  -8.470   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      15.496  -8.470   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      16.266  -7.136   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      17.806  -7.136   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      18.576  -8.470   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      20.116  -8.470   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      17.806  -9.804   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      16.266  -9.804   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      10.106 -15.138   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      10.876 -13.805   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      10.876 -16.472   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      12.416 -16.472   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      13.186 -15.138   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0       5.486 -17.806   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0       6.256 -16.472   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   69                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    9   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   71                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   71                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   66                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   53                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   47   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60   65                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   59                                                       
CONECT   66   43   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68    5   70                                                  
CONECT   70   69                                                            
CONECT   71   31   26   72                                                  
CONECT   72   71                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END

View in JSmol

Synonyms

Value	Source
N-[5-Benzyl-8-(butan-2-yl)-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidate	Generator

Chemical Formula

C₅₁H₇₄N₈O₁₃

Average Mass

1007.1960 Da

Monoisotopic Mass

1006.53753 Da

IUPAC Name

N-[5-benzyl-8-(butan-2-yl)-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-[2-hydroxy-3-(4-hydroxyphenyl)propanamido]pentanediamide

Traditional Name

N-[5-benzyl-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-[2-hydroxy-3-(4-hydroxyphenyl)propanamido]pentanediamide

CAS Registry Number

Not Available

SMILES

CCC(C)C1NC(=O)C(CC2=CC=CC=C2)N(C)C(=O)C(CC(C)C)N2C(O)CCC(NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(O)CC3=CC=C(O)C=C3)C(C)OC1=O)C2=O

InChI Identifier

InChI=1S/C51H74N8O13/c1-9-29(6)42-51(71)72-30(7)43(57-44(64)34(19-21-40(52)62)53-47(67)39(61)26-32-15-17-33(60)18-16-32)48(68)55-36(23-27(2)3)45(65)54-35-20-22-41(63)59(49(35)69)38(24-28(4)5)50(70)58(8)37(46(66)56-42)25-31-13-11-10-12-14-31/h10-18,27-30,34-39,41-43,60-61,63H,9,19-26H2,1-8H3,(H2,52,62)(H,53,67)(H,54,65)(H,55,68)(H,56,66)(H,57,64)

InChI Key

LWLFZSOQVBERAE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
Fatty alcohol ester
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.02	ALOGPS
logP	1.4	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	316.2 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	260.89 m³·mol⁻¹	ChemAxon
Polarizability	104.97 Å³	ChemAxon
Number of Rings	4	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

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Wikipedia Link

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METLIN ID

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PubChem Compound

75274913

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid (NP0314432)

MOL for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

3D MOL for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

3D SDF for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

3D-SDF for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

PDB for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

3D PDB for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

SMILES for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

INCHI for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

Structure for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)

3D Structure for NP0314432 (n-[5-benzyl-6,13,16,21-tetrahydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,9,22-trioxo-8-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}pentanediimidic acid)