NP-MRD: Showing NP-Card for 3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid (NP0185349)

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Record Information

Version

2.0

Created at

2022-09-04 00:43:46 UTC

Updated at

2022-09-04 00:43:47 UTC

NP-MRD ID

NP0185349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid

Description

3-{[2-(Butan-2-yl)-6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,9,22-trioxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]Docosa-6,13,16-trien-12-yl]-C-hydroxycarbonimidoyl}-3-[(1-hydroxyhexylidene)amino]propanoic acid belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. 3-{[2-(Butan-2-yl)-6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,9,22-trioxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]Docosa-6,13,16-trien-12-yl]-C-hydroxycarbonimidoyl}-3-[(1-hydroxyhexylidene)amino]propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191517322D          

 70 73  0  0  0  0            999 V2000
   -3.4551   -7.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7406   -6.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -7.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117   -6.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -7.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1173   -6.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1173   -5.8513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -7.0888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -6.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -5.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -5.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -4.6138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9752   -5.8513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -7.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -7.9138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9752   -6.6763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896   -7.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4615   -6.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1026   -7.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334   -5.8416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582   -5.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575   -5.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960   -6.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5468   -7.1508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5289   -7.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8057   -8.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2343   -8.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9575   -8.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2701   -6.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2880   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0292   -4.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7166   -5.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4931   -9.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9038  -10.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6091  -10.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3324  -10.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0377  -10.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1626  -11.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8680  -12.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7340  -11.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7519  -10.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466  -10.4190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -9.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7878   -9.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3591   -9.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359   -9.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6180  -10.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3233  -10.8159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3054  -11.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5822  -12.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642  -12.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768  -11.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947  -10.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -8.3415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6717   -7.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485   -8.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4752  -10.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0049   -9.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4591   -6.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0056   -5.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3656   -5.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
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 18 20  1  0  0  0  0
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 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 27 28  1  0  0  0  0
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 31 32  2  0  0  0  0
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 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
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 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
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 43 44  1  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
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 54 55  1  0  0  0  0
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 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
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 61 62  2  0  0  0  0
 56 62  1  0  0  0  0
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 63 64  1  0  0  0  0
 17 64  1  0  0  0  0
 64 65  2  0  0  0  0
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 66 67  2  0  0  0  0
 23 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
M  END

     RDKit          3D

139142  0  0  0  0  0  0  0  0999 V2000
   13.2515   -0.6729    2.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9509   -1.1784    1.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9422   -0.6754    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6869   -1.1148   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4448   -0.5972   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2473   -1.0587   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4061   -1.7103   -1.8401 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9733   -0.7867   -0.2936 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7053   -1.1740   -0.8822 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1260   -2.3805   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8604   -2.1741    1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0535   -1.0966    1.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -3.2347    2.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801   -0.0590   -1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2203    1.0725   -1.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2268    1.5607    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7111    0.8841    1.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.7671    0.7300 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958    3.1229    0.6884 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0875    4.5631    0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4673    4.7288   -1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    4.9887   -1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    5.1351   -2.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3389    5.1853   -5.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988    4.7652   -3.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463    4.6207   -2.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    3.1894    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    4.1672    2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4233    3.1214   -1.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1647   -0.8058   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1035   -0.8015   -2.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1490   -2.0678   -0.1760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303   -3.1933   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0581   -2.5169    1.1787 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1724   -3.4809    1.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5232   -2.9448    1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0836   -2.2195    2.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3580   -1.7100    2.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1432   -1.9311    1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4593   -1.4313    1.3677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6344   -2.6449    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4790   -2.8908    1.0938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8220   -2.5122   -0.1575 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.9311   -4.8607   -1.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1843    0.2412   -1.4464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4842    1.2409   -2.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2415    0.4545    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4216   -1.0672    3.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0867   -1.0229    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0316   -2.2820    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004191517322D          

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M  END
> <DATABASE_ID>
NP0185349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)NC(CC(O)=O)C(=O)NC1C(C)OC(=O)C(NC(=O)C(CC2=CC=C(O)C=C2)N(C)C(=O)C(C(C)CC)N2C(O)CCC(NC(=O)C(CC3=CC=C(O)C=C3)NC1=O)C2=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C49H69N7O14/c1-8-10-11-12-37(59)50-35(25-39(61)62)44(64)54-41-28(6)70-49(69)40(26(3)4)53-45(65)36(24-30-15-19-32(58)20-16-30)55(7)48(68)42(27(5)9-2)56-38(60)22-21-33(47(56)67)51-43(63)34(52-46(41)66)23-29-13-17-31(57)18-14-29/h13-20,26-28,33-36,38,40-42,57-58,60H,8-12,21-25H2,1-7H3,(H,50,59)(H,51,63)(H,52,66)(H,53,65)(H,54,64)(H,61,62)

> <INCHI_KEY>
GHKMHLKAFWFBIP-UHFFFAOYSA-N

> <FORMULA>
C49H69N7O14

> <MOLECULAR_WEIGHT>
980.126

> <EXACT_MASS>
979.49024993

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
139

> <JCHEM_AVERAGE_POLARIZABILITY>
100.42117781430159

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[2-(butan-2-yl)-21-hydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]carbamoyl}-3-hexanamidopropanoic acid

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.276084854333333

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20008220560838

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.964358018949509

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958331586759713

> <JCHEM_POLAR_SURFACE_AREA>
310.40999999999997

> <JCHEM_REFRACTIVITY>
250.17920000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hexanamido-3-({21-hydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl}carbamoyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -6.449 -13.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.116 -12.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.782 -13.232   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.448 -12.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.115 -13.232   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.219 -12.462   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.219 -10.922   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       1.553 -13.232   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.886 -12.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.886 -10.922   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.220 -10.152   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.220  -8.612   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.554 -10.922   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.220 -13.232   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.220 -14.772   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       5.554 -12.462   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.887 -13.232   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.328 -12.358   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.525 -13.327   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.836 -10.904   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.375 -10.938   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.307  -9.712   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.819 -12.412   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      12.221 -13.348   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      12.187 -14.888   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.837 -15.629   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.504 -15.687   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.854 -14.946   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.887 -13.406   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.571 -12.607   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.604 -11.068   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.954 -10.327   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.988  -8.787   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.271 -11.126   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.238 -12.665   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      13.471 -17.226   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      12.120 -17.967   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.787 -18.025   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.137 -17.284   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.754 -19.565   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.070 -20.363   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      16.037 -21.903   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.420 -19.623   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.737 -20.421   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      13.404 -20.306   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0      13.370 -21.845   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      14.687 -22.644   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      12.020 -22.586   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.703 -21.787   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.737 -20.248   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0       9.420 -19.449   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0       9.454 -17.909   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      10.804 -17.168   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       8.137 -17.110   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.787 -17.851   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       6.754 -19.391   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.070 -20.190   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.037 -21.729   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.687 -22.470   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       6.653 -24.010   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       5.370 -21.671   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       5.403 -20.132   0.000  0.00  0.00           C+0
HETATM   63  N   UNK     0       8.171 -15.571   0.000  0.00  0.00           N+0
HETATM   64  C   UNK     0       6.854 -14.772   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       5.504 -15.513   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      12.087 -19.507   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      11.209 -18.242   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      12.057 -11.496   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      13.077 -10.343   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      11.882  -9.966   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   64                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   68                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
CONECT   36   27   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   45                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43                                                            
CONECT   45   40   46   66                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   66                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   63                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   62                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   62                                                       
CONECT   62   61   56                                                       
CONECT   63   54   64                                                       
CONECT   64   63   17   65                                                  
CONECT   65   64                                                            
CONECT   66   50   45   67                                                  
CONECT   67   66                                                            
CONECT   68   23   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

View in JSmol

Synonyms

Value	Source
3-{[2-(butan-2-yl)-6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,9,22-trioxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-C-hydroxycarbonimidoyl}-3-[(1-hydroxyhexylidene)amino]propanoate	Generator

Chemical Formula

C₄₉H₆₉N₇O₁₄

Average Mass

980.1260 Da

Monoisotopic Mass

979.49025 Da

IUPAC Name

3-{[2-(butan-2-yl)-21-hydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]carbamoyl}-3-hexanamidopropanoic acid

Traditional Name

3-hexanamido-3-({21-hydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl}carbamoyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)NC(CC(O)=O)C(=O)NC1C(C)OC(=O)C(NC(=O)C(CC2=CC=C(O)C=C2)N(C)C(=O)C(C(C)CC)N2C(O)CCC(NC(=O)C(CC3=CC=C(O)C=C3)NC1=O)C2=O)C(C)C

InChI Identifier

InChI=1S/C49H69N7O14/c1-8-10-11-12-37(59)50-35(25-39(61)62)44(64)54-41-28(6)70-49(69)40(26(3)4)53-45(65)36(24-30-15-19-32(58)20-16-30)55(7)48(68)42(27(5)9-2)56-38(60)22-21-33(47(56)67)51-43(63)34(52-46(41)66)23-29-13-17-31(57)18-14-29/h13-20,26-28,33-36,38,40-42,57-58,60H,8-12,21-25H2,1-7H3,(H,50,59)(H,51,63)(H,52,66)(H,53,65)(H,54,64)(H,61,62)

InChI Key

GHKMHLKAFWFBIP-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 cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Aspartic acid or derivatives
Macrolide lactam
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Macrolactam
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Delta-lactam
Phenol
Piperidinone
N-acyl-amine
Fatty amide
Piperidine
Benzenoid
Dicarboxylic acid or derivatives
Fatty acyl
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Lactam
Lactone
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.23	ALOGPS
logP	2.28	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	310.41 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	250.18 m³·mol⁻¹	ChemAxon
Polarizability	100.42 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

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73837060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid (NP0185349)

MOL for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

3D MOL for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

3D SDF for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

3D-SDF for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

PDB for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

3D PDB for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

SMILES for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

INCHI for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

Structure for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)

3D Structure for NP0185349 (3-[(1-hydroxyhexylidene)amino]-3-({6,13,16,21-tetrahydroxy-5,15-bis[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-2-(sec-butyl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)propanoic acid)