NP-MRD: Showing NP-Card for Oximidine III (NP0005102)

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Record Information

Version

2.0

Created at

2020-12-09 02:26:39 UTC

Updated at

2021-07-15 16:51:03 UTC

NP-MRD ID

NP0005102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oximidine III

Provided By

NPAtlas

Description

(2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0⁶,⁸]Heptadeca-1(13),9,11,14,16-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Oximidine III is found in Pseudomonas and Pseudomonas sp. QN05727. Oximidine III was first documented in 2003 (PMID: 14763554). Based on a literature review very few articles have been published on (2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0⁶,⁸]Heptadeca-1(13),9,11,14,16-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118163D          

 55 57  0  0  0  0            999 V2000
    9.7136   -0.9930   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7613   -1.1701   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7831   -2.1089   -1.6597 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5985   -1.8923   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3658   -0.5931   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2796   -0.1594   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199   -0.9756    0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0031   -2.1796   -0.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612   -0.3993    0.7728 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -1.1481    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6352   -0.6970    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6718   -1.4062    0.5440 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9751    1.3467    2.6458 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.2438    1.8662    2.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4384    1.0709    2.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535    1.2905    2.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0917    2.2983   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
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  7  8  2  0  0  0  0
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  4 35  1  0  0  0  0
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M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
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    1.7546   -1.1481    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118163D          

 55 57  0  0  0  0            999 V2000
    9.7136   -0.9930   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7613   -1.1701   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7831   -2.1089   -1.6597 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6854   -1.3400   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8251    0.0900   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8653   -2.6610   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1889    0.1519   -0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426    0.8745    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0476    0.5825    1.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -2.0624    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    0.2206   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032   -1.6503   -0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5963   -0.9906    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -0.5056    2.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.6482    3.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802    1.7918    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3410    2.7817    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    0.2187    3.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4579    0.5868    2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4071    3.3095    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4595    3.2825   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9643    1.3146   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8622   -0.3132   -3.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7179   -1.3661   -3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4245   -1.5570   -3.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 13  1  0  0  0  0
 17 15  1  0  0  0  0
 28 22  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 13 43  1  1  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 15 46  1  6  0  0  0
 17 47  1  6  0  0  0
 18 48  1  0  0  0  0
 19 49  1  0  0  0  0
 20 50  1  0  0  0  0
 21 51  1  0  0  0  0
 23 52  1  0  0  0  0
 24 53  1  0  0  0  0
 25 54  1  0  0  0  0
 27 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=C([H])C([H])=C1[H])\C([H])=C(\[H])/C(/[H])=C([H])\[C@@]1([H])O[C@@]1([H])C([H])([H])[C@@]([H])(OC2=O)C([H])([H])C(\[H])=C(/[H])N([H])C(=O)C(\[H])=C(\[H])/C(/[H])=N\OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H24N2O6/c1-29-25-14-6-12-21(27)24-13-5-9-17-15-20-19(31-20)11-3-2-7-16-8-4-10-18(26)22(16)23(28)30-17/h2-8,10-14,17,19-20,26H,9,15H2,1H3,(H,24,27)/b7-2-,11-3-,12-6-,13-5+,25-14-/t17-,19+,20-/m0/s1

> <INCHI_KEY>
AHOWOFTYCJCPEK-DELFDNSYSA-N

> <FORMULA>
C23H24N2O6

> <MOLECULAR_WEIGHT>
424.453

> <EXACT_MASS>
424.163436501

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.4173839632542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0^{6,8}]heptadeca-1(17),9,11,13,15-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enamide

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.054696492333333

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.265076823563312

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.670062943967885

> <JCHEM_PKA_STRONGEST_BASIC>
3.783397930350364

> <JCHEM_POLAR_SURFACE_AREA>
109.75000000000001

> <JCHEM_REFRACTIVITY>
118.5451

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0^{6,8}]heptadeca-1(17),9,11,13,15-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    9.7136   -0.9930   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7613   -1.1701   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2796   -0.1594   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199   -0.9756    0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7546   -1.1481    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6352   -0.6970    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6718   -1.4062    0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -0.4604    1.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0028   -0.1514    2.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751    1.3467    2.6458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5277    2.1079    3.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438    1.8662    2.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4384    1.0709    2.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535    1.2905    2.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0312    2.3316    1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917    2.2983   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197    1.2651   -1.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    0.8571   -1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327   -0.0548   -2.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -0.6265   -3.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5935   -0.2775   -2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246   -0.9015   -2.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310    0.6706   -1.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2834    0.8908   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518    1.3118   -1.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.7089    0.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4093   -1.5784    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6854   -1.3400   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8251    0.0900   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8653   -2.6610   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1889    0.1519   -0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426    0.8745    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0476    0.5825    1.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -2.0624    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    0.2206   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032   -1.6503   -0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -2.3542    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -0.9906    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -0.5056    2.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.6482    3.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802    1.7918    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3410    2.7817    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    0.2187    3.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4579    0.5868    2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4071    3.3095    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4595    3.2825   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9643    1.3146   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8622   -0.3132   -3.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7179   -1.3661   -3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4245   -1.5570   -3.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 13  1  0
 17 15  1  0
 28 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 14 45  1  0
 15 46  1  6
 17 47  1  6
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 27 55  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       9.714  -0.993  -0.679  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.761  -1.170  -1.694  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.783  -2.109  -1.660  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.598  -1.892  -1.135  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.366  -0.593  -0.582  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.280  -0.159  -0.017  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.120  -0.976   0.129  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.003  -2.180  -0.257  0.00  0.00           O+0
HETATM    9  N   UNK     0       2.961  -0.399   0.773  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.755  -1.148   0.961  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.635  -0.697   0.405  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.672  -1.406   0.544  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.656  -0.460   1.219  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.003  -0.151   2.576  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.975   1.347   2.646  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.528   2.108   3.612  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.244   1.866   2.302  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.438   1.071   2.641  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.654   1.291   2.190  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.031   2.332   1.293  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.092   2.298  -0.026  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.820   1.265  -1.001  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.973   0.857  -1.742  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.933  -0.055  -2.750  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.742  -0.627  -3.097  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.594  -0.278  -2.426  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.425  -0.902  -2.849  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.631   0.671  -1.373  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.283   0.891  -0.823  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.452   1.312  -1.756  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.850   0.709   0.479  0.00  0.00           O+0
HETATM   32  H   UNK     0       9.409  -1.578   0.197  0.00  0.00           H+0
HETATM   33  H   UNK     0      10.685  -1.340  -1.067  0.00  0.00           H+0
HETATM   34  H   UNK     0       9.825   0.090  -0.395  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.865  -2.661  -1.133  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.189   0.152  -0.627  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.243   0.875   0.367  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.048   0.583   1.091  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.735  -2.062   1.539  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.694   0.221  -0.165  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.003  -1.650  -0.505  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.571  -2.354   1.063  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.596  -0.991   1.477  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.047  -0.506   2.612  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.505  -0.648   3.413  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.080   1.792   2.138  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.341   2.782   1.726  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.333   0.219   3.332  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.458   0.587   2.610  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.407   3.309   1.750  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.460   3.283  -0.494  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.964   1.315  -1.520  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.862  -0.313  -3.265  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.718  -1.366  -3.916  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.425  -1.557  -3.585  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   35                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   38                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   12   40                                                  
CONECT   12   11   13   41   42                                             
CONECT   13   12   14   31   43                                             
CONECT   14   13   15   44   45                                             
CONECT   15   14   16   17   46                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   15   47                                             
CONECT   18   17   19   48                                                  
CONECT   19   18   20   49                                                  
CONECT   20   19   21   50                                                  
CONECT   21   20   22   51                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24   52                                                  
CONECT   24   23   25   53                                                  
CONECT   25   24   26   54                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   55                                                       
CONECT   28   26   29   22                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   13                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
    9.7136   -0.9930   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7613   -1.1701   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7831   -2.1089   -1.6597 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5985   -1.8923   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3658   -0.5931   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2796   -0.1594   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199   -0.9756    0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0031   -2.1796   -0.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612   -0.3993    0.7728 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -1.1481    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6352   -0.6970    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6718   -1.4062    0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -0.4604    1.2194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0028   -0.1514    2.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751    1.3467    2.6458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5277    2.1079    3.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438    1.8662    2.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4384    1.0709    2.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6535    1.2905    2.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0312    2.3316    1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917    2.2983   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197    1.2651   -1.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    0.8571   -1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327   -0.0548   -2.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -0.6265   -3.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5935   -0.2775   -2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246   -0.9015   -2.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310    0.6706   -1.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2834    0.8908   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518    1.3118   -1.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.7089    0.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4093   -1.5784    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6854   -1.3400   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8251    0.0900   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8653   -2.6610   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1889    0.1519   -0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426    0.8745    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0476    0.5825    1.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -2.0624    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    0.2206   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032   -1.6503   -0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -2.3542    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -0.9906    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -0.5056    2.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.6482    3.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802    1.7918    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3410    2.7817    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    0.2187    3.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4579    0.5868    2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4071    3.3095    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4595    3.2825   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9643    1.3146   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8622   -0.3132   -3.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7179   -1.3661   -3.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4245   -1.5570   -3.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 13  1  0
 17 15  1  0
 28 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 14 45  1  0
 15 46  1  6
 17 47  1  6
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 27 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-Hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0,]heptadeca-1(13),9,11,14,16-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidate	Generator

Chemical Formula

C₂₃H₂₄N₂O₆

Average Mass

424.4530 Da

Monoisotopic Mass

424.16344 Da

IUPAC Name

(2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0^{6,8}]heptadeca-1(17),9,11,13,15-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enamide

Traditional Name

(2Z,4Z)-N-[(1E)-3-[(4S,6S,8R,9Z,11Z)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.0^{6,8}]heptadeca-1(17),9,11,13,15-pentaen-4-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enamide

CAS Registry Number

Not Available

SMILES

CO\N=C/C=C\C(=O)N\C=C\C[C@H]1C[C@@H]2O[C@@H]2\C=C/C=C\C2=C(C(O)=CC=C2)C(=O)O1

InChI Identifier

InChI=1S/C23H24N2O6/c1-29-25-14-6-12-21(27)24-13-5-9-17-15-20-19(31-20)11-3-2-7-16-8-4-10-18(26)22(16)23(28)30-17/h2-8,10-14,17,19-20,26H,9,15H2,1H3,(H,24,27)/b7-2-,11-3-,12-6-,13-5+,25-14-/t17-,19+,20-/m0/s1

InChI Key

AHOWOFTYCJCPEK-DELFDNSYSA-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
Pseudomonas	NPAtlas	14763554
Pseudomonas sp. QN05727	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
N-acyl-amine
Benzenoid
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Lactone
Oxime ether
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
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	3.19	ALOGPS
logP	3.05	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	3.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.55 m³·mol⁻¹	ChemAxon
Polarizability	44.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA001223

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

101268765

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hayakawa Y, Tomikawa T, Shin-ya K, Arao N, Nagai K, Suzuki K: Oximidine III, a new antitumor antibiotic against transformed cells from Pseudomonas sp. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity. J Antibiot (Tokyo). 2003 Nov;56(11):899-904. doi: 10.7164/antibiotics.56.899. [PubMed:14763554 ]

Showing NP-Card for Oximidine III (NP0005102)

MOL for NP0005102 (Oximidine III)

3D MOL for NP0005102 (Oximidine III)

3D SDF for NP0005102 (Oximidine III)

3D-SDF for NP0005102 (Oximidine III)

PDB for NP0005102 (Oximidine III)

3D PDB for NP0005102 (Oximidine III)

SMILES for NP0005102 (Oximidine III)

INCHI for NP0005102 (Oximidine III)

Structure for NP0005102 (Oximidine III)

3D Structure for NP0005102 (Oximidine III)