NP-MRD: Showing NP-Card for Haliangicin (NP0003646)

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Record Information

Version

2.0

Created at

2020-12-09 00:50:15 UTC

Updated at

2021-07-15 16:46:59 UTC

NP-MRD ID

NP0003646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haliangicin

Provided By

NPAtlas

Description

Haliangicin is found in Haliangium and Haliangium luteum. Haliangicin was first documented in 2001 (PMID: 11302487). Based on a literature review very few articles have been published on methyl (2E,6Z,8E)-11-(3-ethenyl-2-methyloxiran-2-yl)-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

 59 59  0  0  0  0            999 V2000
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    3.2652   -0.3743    2.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117493D          

 59 59  0  0  0  0            999 V2000
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    5.8282    3.2913    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9301    1.9397   -2.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9866    0.7715   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665   -1.7997    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8145   -0.2088    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -0.7555    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    0.8947   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366    1.6207    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395    0.8454    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262   -0.5263    3.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -1.3252    2.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    0.4935    3.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -2.6387   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -3.1889    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -2.6662    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3234    0.1999    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743   -2.8209   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -3.7780   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -2.9196   -2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437   -2.9145   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    0.3590    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    0.2039   -2.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -1.5824   -3.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -0.8267   -2.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1697    2.7662    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4519   -0.6035   -2.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5871   -1.8445   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2537   -0.2069   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    3.8412    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    3.0885    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6827    4.0806    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 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
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5  3  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2 30  1  0  0  0  0
  3 31  1  1  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  1  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
 12 44  1  0  0  0  0
 13 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 16 49  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 21 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 27 57  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])[C@]1([H])O[C@]1(C([H])([H])[H])C([H])([H])[C@@]([H])(C(=C(/[H])\C(\[H])=C(/C(/[H])=C(\OC([H])([H])[H])/C(/OC([H])([H])[H])=C(/[H])C(=O)OC([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-9-20-22(5,27-20)14-17(4)16(3)11-10-15(2)12-18(24-6)19(25-7)13-21(23)26-8/h9-13,17,20H,1,14H2,2-8H3/b15-10-,16-11+,18-12-,19-13+/t17-,20-,22+/m0/s1

> <INCHI_KEY>
XIKGETOZQXNXHV-CPFPKWEUSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.493

> <EXACT_MASS>
376.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.377083548650106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,4Z,6Z,8E,10S)-11-[(2R,3S)-3-ethenyl-2-methyloxiran-2-yl]-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoate

> <ALOGPS_LOGP>
5.21

> <JCHEM_LOGP>
3.5935802223333324

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.085391171478954

> <JCHEM_POLAR_SURFACE_AREA>
57.290000000000006

> <JCHEM_REFRACTIVITY>
112.14359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4Z,6Z,8E,10S)-11-[(2R,3S)-3-ethenyl-2-methyloxiran-2-yl]-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 59  0  0  0  0  0  0  0  0999 V2000
    5.4075    3.1847   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682    1.9991   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9070    0.7671   -0.5898 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3506   -0.4571   -0.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0109   -0.0741    0.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8458   -0.7277    1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7615    0.6374    0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601   -0.0096    1.5441 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2652   -0.3743    2.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   -1.0547    0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -2.4383    0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -0.8093    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1392   -1.8509   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -1.6439   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754   -2.8342   -1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471   -0.4117   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -0.0465   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9935   -0.9748   -1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.8321   -2.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7467    1.2571   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364    1.6905   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0188    0.9795   -0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1047    1.7159   -0.9773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2263   -0.2613   -1.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4102   -0.7725   -1.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460    2.1633    0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796    3.3327    1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0029    4.0557   -1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282    3.2913    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9301    1.9397   -2.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9866    0.7715   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665   -1.7997    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8145   -0.2088    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -0.7555    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    0.8947   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366    1.6207    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395    0.8454    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262   -0.5263    3.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -1.3252    2.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    0.4935    3.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -2.6387   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -3.1889    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -2.6662    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3234    0.1999    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743   -2.8209   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -3.7780   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -2.9196   -2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437   -2.9145   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    0.3590    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    0.2039   -2.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -1.5824   -3.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -0.8267   -2.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1697    2.7662    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4519   -0.6035   -2.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5871   -1.8445   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2537   -0.2069   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    3.8412    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    3.0885    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6827    4.0806    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
  5  3  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  3 31  1  1
  6 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  1
  9 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 21 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  0
 27 58  1  0
 27 59  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       5.407   3.185  -0.550  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.368   1.999  -1.193  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.907   0.767  -0.590  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.351  -0.457  -0.946  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.011  -0.074   0.339  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.846  -0.728   1.424  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.761   0.637   0.671  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.760  -0.010   1.544  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.265  -0.374   2.935  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.937  -1.055   0.932  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.405  -2.438   0.666  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.653  -0.809   0.565  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.139  -1.851  -0.035  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.421  -1.644  -0.410  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.075  -2.834  -1.011  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.047  -0.412  -0.133  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.270  -0.047  -0.468  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.994  -0.975  -1.178  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.749  -0.832  -2.628  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.747   1.257  -0.092  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.936   1.690  -0.278  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.019   0.980  -0.865  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.105   1.716  -0.977  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.226  -0.261  -1.330  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.410  -0.773  -1.874  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.846   2.163   0.540  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.280   3.333   1.159  0.00  0.00           C+0
HETATM   28  H   UNK     0       5.003   4.056  -1.028  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.828   3.291   0.424  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.930   1.940  -2.182  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.987   0.772  -0.453  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.566  -1.800   1.447  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.814  -0.209   2.381  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.945  -0.756   1.153  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.248   0.895  -0.285  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.037   1.621   1.117  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.039   0.845   1.793  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.326  -0.526   3.549  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.786  -1.325   2.977  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.753   0.494   3.370  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.294  -2.639  -0.420  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.724  -3.189   1.170  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.393  -2.666   1.058  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.323   0.200   0.761  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.274  -2.821  -0.202  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.562  -3.778  -0.616  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.944  -2.920  -2.099  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.144  -2.914  -0.753  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.472   0.359   0.441  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.094   0.204  -2.934  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.277  -1.582  -3.193  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.683  -0.827  -2.847  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.170   2.766   0.061  0.00  0.00           H+0
HETATM   54  H   UNK     0      -7.452  -0.604  -2.969  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.587  -1.845  -1.604  0.00  0.00           H+0
HETATM   56  H   UNK     0      -8.254  -0.207  -1.415  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.357   3.841   1.572  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.000   3.088   1.962  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.683   4.081   0.434  0.00  0.00           H+0
CONECT    1    2   28   29                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5   31                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7    3                                             
CONECT    6    5   32   33   34                                             
CONECT    7    5    8   35   36                                             
CONECT    8    7    9   10   37                                             
CONECT    9    8   38   39   40                                             
CONECT   10    8   11   12                                                  
CONECT   11   10   41   42   43                                             
CONECT   12   10   13   44                                                  
CONECT   13   12   14   45                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   46   47   48                                             
CONECT   16   14   17   49                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   50   51   52                                             
CONECT   20   17   21   26                                                  
CONECT   21   20   22   53                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   54   55   56                                             
CONECT   26   20   27                                                       
CONECT   27   26   57   58   59                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   21                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  118    0
END

RDKit          3D

59 59  0  0  0  0  0  0  0  0999 V2000
    5.4075    3.1847   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682    1.9991   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9070    0.7671   -0.5898 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3506   -0.4571   -0.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0109   -0.0741    0.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8458   -0.7277    1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7615    0.6374    0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601   -0.0096    1.5441 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2652   -0.3743    2.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   -1.0547    0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -2.4383    0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -0.8093    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1392   -1.8509   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -1.6439   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754   -2.8342   -1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471   -0.4117   -0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -0.0465   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9935   -0.9748   -1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.8321   -2.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7467    1.2571   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364    1.6905   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0188    0.9795   -0.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1047    1.7159   -0.9773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2263   -0.2613   -1.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4102   -0.7725   -1.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460    2.1633    0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796    3.3327    1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0029    4.0557   -1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282    3.2913    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9301    1.9397   -2.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9866    0.7715   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665   -1.7997    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8145   -0.2088    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -0.7555    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    0.8947   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366    1.6207    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395    0.8454    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262   -0.5263    3.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -1.3252    2.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    0.4935    3.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -2.6387   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -3.1889    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -2.6662    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3234    0.1999    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743   -2.8209   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -3.7780   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -2.9196   -2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437   -2.9145   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    0.3590    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    0.2039   -2.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -1.5824   -3.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -0.8267   -2.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1697    2.7662    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4519   -0.6035   -2.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5871   -1.8445   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2537   -0.2069   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    3.8412    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    3.0885    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6827    4.0806    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
  5  3  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  3 31  1  1
  6 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  1
  9 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 21 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (2E,6Z,8E)-11-(3-ethenyl-2-methyloxiran-2-yl)-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoic acid	Generator

Chemical Formula

C₂₂H₃₂O₅

Average Mass

376.4930 Da

Monoisotopic Mass

376.22497 Da

IUPAC Name

methyl (2E,4Z,6Z,8E,10S)-11-[(2R,3S)-3-ethenyl-2-methyloxiran-2-yl]-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoate

Traditional Name

methyl (2E,4Z,6Z,8E,10S)-11-[(2R,3S)-3-ethenyl-2-methyloxiran-2-yl]-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C(\OC)/C(/OC)=C/C(/C)=C\C=C(/C)C(C)CC1(C)OC1C=C

InChI Identifier

InChI=1S/C22H32O5/c1-9-20-22(5,27-20)14-17(4)16(3)11-10-15(2)12-18(24-6)19(25-7)13-21(23)26-8/h9-13,17,20H,1,14H2,2-8H3/b15-10-,16-11+,18-12-,19-13+

InChI Key

XIKGETOZQXNXHV-CPFPKWEUSA-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
Haliangium	NPAtlas	11302487
Haliangium luteum	-	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	5.21	ALOGPS
logP	3.59	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.29 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	112.14 m³·mol⁻¹	ChemAxon
Polarizability	43.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA007321

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8266487

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10090950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fudou R, Iizuka T, Yamanaka S: Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium. 1. Fermentation and biological characteristics. J Antibiot (Tokyo). 2001 Feb;54(2):149-52. doi: 10.7164/antibiotics.54.149. [PubMed:11302487 ]

Showing NP-Card for Haliangicin (NP0003646)

MOL for NP0003646 (Haliangicin)

3D MOL for NP0003646 (Haliangicin)

3D SDF for NP0003646 (Haliangicin)

3D-SDF for NP0003646 (Haliangicin)

PDB for NP0003646 (Haliangicin)

3D PDB for NP0003646 (Haliangicin)

SMILES for NP0003646 (Haliangicin)

INCHI for NP0003646 (Haliangicin)

Structure for NP0003646 (Haliangicin)

3D Structure for NP0003646 (Haliangicin)