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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014964

Secondary Accession Numbers

HMDB0030468
HMDB14964
HMDB30468

Metabolite Identification

Common Name

Natamycin

Description

Natamycin is only found in individuals that have used or taken this drug. It is an amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. [PubChem]Like other polyene antibiotics, Natamycin inhibits fungal growth by binding to sterols. Specifically, Natamycin binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission. This differs from the mechanism of most other polyene antibiotics, which tend to work by altering fungal membrane permeability instead.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

LS-7662
  Mrv0541 02231215022D          

 47 50  0  0  0  0            999 V2000
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    0.3713   -1.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7724   -3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -1.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0014964
     RDKit          3D
Natamycin
 94 97  0  0  0  0  0  0  0  0999 V2000
    5.2890    2.2608    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038    1.9484   -0.9812 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

LS-7662
  Mrv0541 02231215022D          

 47 50  0  0  0  0            999 V2000
   -1.0587   -2.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713   -2.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713   -1.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874   -2.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724   -3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -1.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -2.6799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2024   -3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6310   -0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6310   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9174    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0587    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724    1.0313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3713    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0574   -0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724   -0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7724    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574    1.0313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0574   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6310   -3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3460   -1.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574    1.8563    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3713    2.2399    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3437    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    2.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    3.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    3.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -0.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160   -0.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310   -0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6310    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9160    1.0313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2010    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4874    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 18 19  1  0  0  0  0
 16 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 18 23  1  0  0  0  0
  4 24  1  0  0  0  0
 20 24  2  0  0  0  0
  8 25  1  1  0  0  0
 12 26  2  0  0  0  0
 14 27  1  0  0  0  0
 15 27  1  1  0  0  0
 17 28  1  6  0  0  0
 19 29  1  1  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 19 32  1  0  0  0  0
 30 33  1  1  0  0  0
 31 34  1  6  0  0  0
 33 35  1  0  0  0  0
 33 36  2  0  0  0  0
 21 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  1  0  0  0
 42 45  1  1  0  0  0
 41 46  1  6  0  0  0
 40 47  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0014964

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1

> <INCHI_KEY>
NCXMLFZGDNKEPB-BQGNJOPGSA-N

> <FORMULA>
C33H47NO13

> <MOLECULAR_WEIGHT>
665.7252

> <EXACT_MASS>
665.304740595

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
68.19403432107165

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

> <ALOGPS_LOGP>
-3.46

> <JCHEM_LOGP>
-1.694913093638562

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.830297037788116

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.579739281946898

> <JCHEM_PKA_STRONGEST_BASIC>
9.113107009890703

> <JCHEM_POLAR_SURFACE_AREA>
230.98999999999998

> <JCHEM_REFRACTIVITY>
169.88260000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
natamycin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014964
     RDKit          3D
Natamycin
 94 97  0  0  0  0  0  0  0  0999 V2000
    5.2890    2.2608    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038    1.9484   -0.9812 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7144    2.2758   -1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    3.5970   -0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120    4.5945   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    4.5859   -2.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    4.2003   -2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    4.1417   -1.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2110    3.4408   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    2.1121   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173    0.9995   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2605    0.2111   -0.7170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1725    0.9916   -0.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477    1.2242   -0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    0.6108    0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445    1.1973    1.2508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4954    0.4726    2.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9250    2.6514    1.0411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2203    3.2574    2.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7988    3.3746    0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1977    4.7551    0.1642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6843    2.6543   -1.0345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9800    2.7199   -1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8409   -0.9556    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8334   -2.0950    0.1821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5835   -2.9153    1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -3.9495    1.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2254   -4.9663    1.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -3.6102    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -4.1855    0.7993 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0642   -3.2895   -0.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -4.4059    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8365   -3.1928    1.8641 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2867   -3.5245    1.8303 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6026   -2.5205    0.9344 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0783   -1.1841    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -0.5335    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.1714   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4260   -0.6230   -1.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4510    0.6159   -1.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505   -4.5926   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0659   -4.2301   -0.9671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1576   -4.9093   -2.1641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -2.7295   -1.1456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3492   -2.3725   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600   -1.7981   -2.8656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199   -2.6821   -1.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.7041    1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745    3.3599    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550    1.9667    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8400    2.6061   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    1.4539   -1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    2.3424   -2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    3.6941    0.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240    5.5933   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997    4.9655   -3.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844    3.8682   -3.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665    4.7312   -1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715    3.9141    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    2.0428    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    0.5404   -1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890   -0.1556   -1.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290    0.6854   -1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386    1.1683    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211   -0.3351    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3401   -0.0010    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9761    1.1602    2.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8275    2.6846    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4827    3.8547    2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769    3.2501    0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3906    5.3293    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    5.0255   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0210    3.1166   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368    2.3600   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.5924    1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -1.3882   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245   -1.6001    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -4.8706    2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -4.0535    2.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -2.5359    1.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968   -5.1357    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890   -2.3861    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -4.9578    2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289   -5.1750    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -2.7516    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820   -2.8629   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153   -0.6831    2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9430   -0.2062    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458   -4.2661   -0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393   -5.7017   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356   -4.4563   -0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -5.6486   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -2.4258   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010   -2.6844   -0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 12 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 27 41  1  0
 41 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 45 46  2  0
 45 47  1  0
 40  2  1  0
 22 14  1  0
 44 25  1  0
 35 33  1  0
  1 48  1  0
  1 49  1  0
  1 50  1  0
  2 51  1  6
  3 52  1  0
  3 53  1  0
  4 54  1  0
  5 55  1  0
  6 56  1  0
  7 57  1  0
  8 58  1  0
  9 59  1  0
 10 60  1  0
 11 61  1  0
 12 62  1  6
 14 63  1  0
 16 64  1  1
 17 65  1  0
 17 66  1  0
 17 67  1  0
 18 68  1  6
 19 69  1  0
 20 70  1  1
 21 71  1  0
 21 72  1  0
 22 73  1  6
 23 74  1  0
 24 75  1  0
 24 76  1  0
 25 77  1  1
 28 78  1  0
 29 79  1  0
 29 80  1  0
 30 81  1  6
 31 82  1  0
 32 83  1  0
 32 84  1  0
 33 85  1  1
 35 86  1  6
 36 87  1  0
 37 88  1  0
 41 89  1  0
 41 90  1  0
 42 91  1  1
 43 92  1  0
 44 93  1  6
 47 94  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LS-7662                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.976  -5.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.642  -5.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.693  -5.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.693  -3.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.643  -5.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.308  -5.772   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.312  -3.462   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.312  -5.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.978  -5.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.312  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.645  -1.152   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.645  -2.692   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.643   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.978   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.312   1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.976   1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.308   1.925   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.693   1.155   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.642   1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.974  -1.152   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.308  -0.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.308   1.155   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.974   1.925   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.974  -2.692   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.645  -5.772   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.979  -3.462   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.312   2.695   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.308   3.465   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.642   0.385   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.974   3.465   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.693   4.181   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.642   3.465   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.308   4.232   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.693   5.721   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.643   3.465   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.308   5.772   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.643  -1.152   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.975  -0.385   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.310  -1.152   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       8.645  -0.385   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.645   1.155   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.310   1.925   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.975   1.155   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.643   1.925   0.000  0.00  0.00           O+0
HETATM   45  N   UNK     0       7.310   3.465   0.000  0.00  0.00           N+0
HETATM   46  O   UNK     0       9.979   1.925   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       9.979  -1.152   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3   24                                                       
CONECT    5    6    9                                                       
CONECT    6    5    1                                                       
CONECT    7    8   12                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8    5                                                       
CONECT   10   11   15                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   26                                                  
CONECT   13   14   17                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   10   27                                                  
CONECT   16   17   19                                                       
CONECT   17   16   13   28                                                  
CONECT   18   19   23                                                       
CONECT   19   18   16   29   32                                             
CONECT   20   21   24                                                       
CONECT   21   20   22   37                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   30                                                  
CONECT   24    4   20                                                       
CONECT   25    8                                                            
CONECT   26   12                                                            
CONECT   27   14   15                                                       
CONECT   28   17                                                            
CONECT   29   19                                                            
CONECT   30   23   31   33                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   19                                                       
CONECT   33   30   35   36                                                  
CONECT   34   31                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   21   38                                                       
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   47                                                  
CONECT   41   40   42   46                                                  
CONECT   42   41   43   45                                                  
CONECT   43   42   38   44                                                  
CONECT   44   43                                                            
CONECT   45   42                                                            
CONECT   46   41                                                            
CONECT   47   40                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

COMPND    HMDB0014964
HETATM    1  C1  UNL     1       5.289   2.261   0.488  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.104   1.948  -0.981  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.714   2.276  -1.482  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.264   3.597  -0.978  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.812   4.595  -1.683  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.856   4.586  -2.777  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.603   4.200  -2.732  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.324   4.142  -1.639  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.211   3.441  -0.509  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.345   2.112  -0.375  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.017   1.000  -0.964  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.261   0.211  -0.717  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.173   0.992  -0.086  1.00  0.00           O  
HETATM   14  C13 UNL     1      -3.348   1.224  -0.707  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.385   0.611   0.008  1.00  0.00           O  
HETATM   16  C14 UNL     1      -4.545   1.197   1.251  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.495   0.473   2.137  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.925   2.651   1.041  1.00  0.00           C  
HETATM   19  O3  UNL     1      -5.220   3.257   2.242  1.00  0.00           O  
HETATM   20  C17 UNL     1      -3.799   3.375   0.295  1.00  0.00           C  
HETATM   21  N1  UNL     1      -4.198   4.755   0.164  1.00  0.00           N  
HETATM   22  C18 UNL     1      -3.684   2.654  -1.034  1.00  0.00           C  
HETATM   23  O4  UNL     1      -4.980   2.720  -1.605  1.00  0.00           O  
HETATM   24  C19 UNL     1      -0.841  -0.956   0.169  1.00  0.00           C  
HETATM   25  C20 UNL     1      -1.833  -2.095   0.182  1.00  0.00           C  
HETATM   26  O5  UNL     1      -1.584  -2.915   1.251  1.00  0.00           O  
HETATM   27  C21 UNL     1      -0.715  -3.949   1.111  1.00  0.00           C  
HETATM   28  O6  UNL     1      -1.225  -4.966   1.966  1.00  0.00           O  
HETATM   29  C22 UNL     1       0.638  -3.610   1.601  1.00  0.00           C  
HETATM   30  C23 UNL     1       1.771  -4.185   0.799  1.00  0.00           C  
HETATM   31  O7  UNL     1       2.064  -3.290  -0.227  1.00  0.00           O  
HETATM   32  C24 UNL     1       3.039  -4.406   1.554  1.00  0.00           C  
HETATM   33  C25 UNL     1       3.837  -3.193   1.864  1.00  0.00           C  
HETATM   34  O8  UNL     1       5.287  -3.525   1.830  1.00  0.00           O  
HETATM   35  C26 UNL     1       4.603  -2.521   0.934  1.00  0.00           C  
HETATM   36  C27 UNL     1       5.078  -1.184   1.356  1.00  0.00           C  
HETATM   37  C28 UNL     1       6.119  -0.534   0.869  1.00  0.00           C  
HETATM   38  C29 UNL     1       6.338  -0.171  -0.529  1.00  0.00           C  
HETATM   39  O9  UNL     1       7.426  -0.623  -1.065  1.00  0.00           O  
HETATM   40  O10 UNL     1       5.451   0.616  -1.285  1.00  0.00           O  
HETATM   41  C30 UNL     1      -0.750  -4.593  -0.257  1.00  0.00           C  
HETATM   42  C31 UNL     1      -2.066  -4.230  -0.967  1.00  0.00           C  
HETATM   43  O11 UNL     1      -2.158  -4.909  -2.164  1.00  0.00           O  
HETATM   44  C32 UNL     1      -2.021  -2.730  -1.146  1.00  0.00           C  
HETATM   45  C33 UNL     1      -3.349  -2.373  -1.755  1.00  0.00           C  
HETATM   46  O12 UNL     1      -3.460  -1.798  -2.866  1.00  0.00           O  
HETATM   47  O13 UNL     1      -4.520  -2.682  -1.080  1.00  0.00           O  
HETATM   48  H1  UNL     1       4.622   1.704   1.143  1.00  0.00           H  
HETATM   49  H2  UNL     1       5.275   3.360   0.641  1.00  0.00           H  
HETATM   50  H3  UNL     1       6.355   1.967   0.722  1.00  0.00           H  
HETATM   51  H4  UNL     1       5.840   2.606  -1.530  1.00  0.00           H  
HETATM   52  H5  UNL     1       3.009   1.454  -1.251  1.00  0.00           H  
HETATM   53  H6  UNL     1       3.799   2.342  -2.594  1.00  0.00           H  
HETATM   54  H7  UNL     1       3.339   3.694   0.122  1.00  0.00           H  
HETATM   55  H8  UNL     1       3.224   5.593  -1.403  1.00  0.00           H  
HETATM   56  H9  UNL     1       2.300   4.966  -3.740  1.00  0.00           H  
HETATM   57  H10 UNL     1       0.184   3.868  -3.708  1.00  0.00           H  
HETATM   58  H11 UNL     1      -1.266   4.731  -1.695  1.00  0.00           H  
HETATM   59  H12 UNL     1      -0.572   3.914   0.431  1.00  0.00           H  
HETATM   60  H13 UNL     1       1.219   2.043   0.334  1.00  0.00           H  
HETATM   61  H14 UNL     1       0.649   0.540  -1.729  1.00  0.00           H  
HETATM   62  H15 UNL     1      -1.589  -0.156  -1.720  1.00  0.00           H  
HETATM   63  H16 UNL     1      -3.329   0.685  -1.701  1.00  0.00           H  
HETATM   64  H17 UNL     1      -3.539   1.168   1.753  1.00  0.00           H  
HETATM   65  H18 UNL     1      -5.021  -0.335   2.744  1.00  0.00           H  
HETATM   66  H19 UNL     1      -6.340  -0.001   1.600  1.00  0.00           H  
HETATM   67  H20 UNL     1      -5.976   1.160   2.882  1.00  0.00           H  
HETATM   68  H21 UNL     1      -5.828   2.685   0.384  1.00  0.00           H  
HETATM   69  H22 UNL     1      -4.483   3.855   2.530  1.00  0.00           H  
HETATM   70  H23 UNL     1      -2.877   3.250   0.899  1.00  0.00           H  
HETATM   71  H24 UNL     1      -3.391   5.329   0.493  1.00  0.00           H  
HETATM   72  H25 UNL     1      -4.458   5.025  -0.797  1.00  0.00           H  
HETATM   73  H26 UNL     1      -3.021   3.117  -1.754  1.00  0.00           H  
HETATM   74  H27 UNL     1      -4.937   2.360  -2.541  1.00  0.00           H  
HETATM   75  H28 UNL     1      -0.678  -0.592   1.201  1.00  0.00           H  
HETATM   76  H29 UNL     1       0.120  -1.388  -0.179  1.00  0.00           H  
HETATM   77  H30 UNL     1      -2.825  -1.600   0.435  1.00  0.00           H  
HETATM   78  H31 UNL     1      -0.790  -4.871   2.870  1.00  0.00           H  
HETATM   79  H32 UNL     1       0.766  -4.054   2.634  1.00  0.00           H  
HETATM   80  H33 UNL     1       0.853  -2.536   1.759  1.00  0.00           H  
HETATM   81  H34 UNL     1       1.497  -5.136   0.293  1.00  0.00           H  
HETATM   82  H35 UNL     1       2.289  -2.386   0.091  1.00  0.00           H  
HETATM   83  H36 UNL     1       2.828  -4.958   2.520  1.00  0.00           H  
HETATM   84  H37 UNL     1       3.629  -5.175   0.967  1.00  0.00           H  
HETATM   85  H38 UNL     1       3.650  -2.752   2.889  1.00  0.00           H  
HETATM   86  H39 UNL     1       4.782  -2.863  -0.097  1.00  0.00           H  
HETATM   87  H40 UNL     1       4.515  -0.683   2.160  1.00  0.00           H  
HETATM   88  H41 UNL     1       6.943  -0.206   1.550  1.00  0.00           H  
HETATM   89  H42 UNL     1       0.046  -4.266  -0.934  1.00  0.00           H  
HETATM   90  H43 UNL     1      -0.739  -5.702  -0.227  1.00  0.00           H  
HETATM   91  H44 UNL     1      -2.936  -4.456  -0.310  1.00  0.00           H  
HETATM   92  H45 UNL     1      -2.821  -5.649  -2.033  1.00  0.00           H  
HETATM   93  H46 UNL     1      -1.265  -2.426  -1.900  1.00  0.00           H  
HETATM   94  H47 UNL     1      -4.601  -2.684  -0.074  1.00  0.00           H  
CONECT    1    2   48   49   50
CONECT    2    3   40   51
CONECT    3    4   52   53
CONECT    4    5    5   54
CONECT    5    6   55
CONECT    6    7    7   56
CONECT    7    8   57
CONECT    8    9    9   58
CONECT    9   10   59
CONECT   10   11   11   60
CONECT   11   12   61
CONECT   12   13   24   62
CONECT   13   14
CONECT   14   15   22   63
CONECT   15   16
CONECT   16   17   18   64
CONECT   17   65   66   67
CONECT   18   19   20   68
CONECT   19   69
CONECT   20   21   22   70
CONECT   21   71   72
CONECT   22   23   73
CONECT   23   74
CONECT   24   25   75   76
CONECT   25   26   44   77
CONECT   26   27
CONECT   27   28   29   41
CONECT   28   78
CONECT   29   30   79   80
CONECT   30   31   32   81
CONECT   31   82
CONECT   32   33   83   84
CONECT   33   34   35   85
CONECT   34   35
CONECT   35   36   86
CONECT   36   37   37   87
CONECT   37   38   88
CONECT   38   39   39   40
CONECT   41   42   89   90
CONECT   42   43   44   91
CONECT   43   92
CONECT   44   45   93
CONECT   45   46   46   47
CONECT   47   94
END

HMDB0014964
     RDKit          3D
Natamycin
 94 97  0  0  0  0  0  0  0  0999 V2000
    5.2890    2.2608    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038    1.9484   -0.9812 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7144    2.2758   -1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    3.5970   -0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120    4.5945   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    4.5859   -2.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    4.2003   -2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    4.1417   -1.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2110    3.4408   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    2.1121   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173    0.9995   -0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2605    0.2111   -0.7170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1725    0.9916   -0.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477    1.2242   -0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    0.6108    0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445    1.1973    1.2508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4954    0.4726    2.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9250    2.6514    1.0411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2203    3.2574    2.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7988    3.3746    0.2948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1977    4.7551    0.1642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6843    2.6543   -1.0345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9800    2.7199   -1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8409   -0.9556    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8334   -2.0950    0.1821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5835   -2.9153    1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -3.9495    1.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2254   -4.9663    1.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -3.6102    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -4.1855    0.7993 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0642   -3.2895   -0.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -4.4059    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8365   -3.1928    1.8641 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2867   -3.5245    1.8303 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6026   -2.5205    0.9344 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0783   -1.1841    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -0.5335    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.1714   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4260   -0.6230   -1.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4510    0.6159   -1.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505   -4.5926   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0659   -4.2301   -0.9671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1576   -4.9093   -2.1641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -2.7295   -1.1456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3492   -2.3725   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4600   -1.7981   -2.8656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199   -2.6821   -1.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.7041    1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745    3.3599    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550    1.9667    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8400    2.6061   -1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    1.4539   -1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    2.3424   -2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    3.6941    0.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240    5.5933   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997    4.9655   -3.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844    3.8682   -3.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665    4.7312   -1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715    3.9141    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    2.0428    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    0.5404   -1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890   -0.1556   -1.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290    0.6854   -1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386    1.1683    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211   -0.3351    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3401   -0.0010    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9761    1.1602    2.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8275    2.6846    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4827    3.8547    2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769    3.2501    0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3906    5.3293    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    5.0255   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0210    3.1166   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368    2.3600   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.5924    1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -1.3882   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245   -1.6001    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -4.8706    2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -4.0535    2.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -2.5359    1.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968   -5.1357    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890   -2.3861    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -4.9578    2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289   -5.1750    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -2.7516    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820   -2.8629   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153   -0.6831    2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9430   -0.2062    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458   -4.2661   -0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393   -5.7017   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356   -4.4563   -0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -5.6486   -2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -2.4258   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010   -2.6844   -0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 12 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
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 37 38  1  0
 38 39  2  0
 38 40  1  0
 27 41  1  0
 41 42  1  0
 42 43  1  0
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 44 45  1  0
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 45 47  1  0
 40  2  1  0
 22 14  1  0
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 35 33  1  0
  1 48  1  0
  1 49  1  0
  1 50  1  0
  2 51  1  6
  3 52  1  0
  3 53  1  0
  4 54  1  0
  5 55  1  0
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 33 85  1  1
 35 86  1  6
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 37 88  1  0
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 43 92  1  0
 44 93  1  6
 47 94  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Pimaricin	Kegg
Natacyn	Kegg
PMR	KEGG
a 5283	HMDB
Antibiotic a 5283	HMDB
Antibiotic a-5283	HMDB
CL 12625	HMDB
Delvocid	HMDB
Delvolan	HMDB
Delvopos	HMDB
e235	HMDB
Mycophyt	HMDB
Myprozine	HMDB, MeSH
Natafucin	HMDB
Pimafucin	HMDB, MeSH
Pimafugin	HMDB
Pimaricin (JP15)	HMDB
Pimaricine	HMDB
Synogil	HMDB
Tennecetin	HMDB, MeSH
Tymasil	HMDB

Chemical Formula

C₃₃H₄₇NO₁₃

Average Molecular Weight

665.7252

Monoisotopic Molecular Weight

665.304740595

IUPAC Name

(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

Traditional Name

natamycin

CAS Registry Number

7681-93-8

SMILES

C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O

InChI Identifier

InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1

InChI Key

NCXMLFZGDNKEPB-BQGNJOPGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Dicarboxylic acid or derivatives
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Hemiacetal
Secondary alcohol
Carboxylic acid ester
Amino acid
Amino acid or derivatives
1,2-aminoalcohol
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Dialkyl ether
Organoheterocyclic compound
Oxirane
Ether
Polyol
Alcohol
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Carbonyl group
Organonitrogen compound
Primary aliphatic amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

antibiotic antifungal drug (CHEBI:7488 )
macrolide (CHEBI:7488 )
Antibiotic fungicides (C08073 )

Ontology

Not Available

Blood (HMDB: HMDB0014964)
Urine (HMDB: HMDB0014964)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014964)
Extracellular (HMDB: HMDB0014964)

Source

Endogenous

Endogenous (HMDB: HMDB0014964)

Exogenous

Food

Food (HMDB: HMDB0014964)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antibacterial (HMDB: HMDB0014964)

Antimycotic (HMDB: HMDB0014964)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	952.17 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.28 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-1.7	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	230.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	169.88 m³·mol⁻¹	ChemAxon
Polarizability	68.19 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	248.835	30932474
DeepCCS	[M-H]-	246.988	30932474
DeepCCS	[M-2H]-	281.023	30932474
DeepCCS	[M+Na]+	255.041	30932474
AllCCS	[M+H]+	258.8	32859911
AllCCS	[M+H-H2O]+	257.6	32859911
AllCCS	[M+NH4]+	259.9	32859911
AllCCS	[M+Na]+	260.2	32859911
AllCCS	[M-H]-	261.8	32859911
AllCCS	[M+Na-2H]-	266.5	32859911
AllCCS	[M+HCOO]-	271.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Natamycin	C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O	6287.5	Standard polar	33892256
Natamycin	C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O	5082.6	Standard non polar	33892256
Natamycin	C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O	5302.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-9200015000-f595a5ec647350aa5e44	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 10V, Positive-QTOF	splash10-0ul1-0000159000-db7c73a2c6e943055873	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 20V, Positive-QTOF	splash10-0udi-0300292000-e96b0296247cf041eb27	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 40V, Positive-QTOF	splash10-0f6t-0509350000-4c2c7b4ac6bdbd8f7641	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 10V, Negative-QTOF	splash10-0w9a-2000139000-12a04d582d7eb949cc7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 20V, Negative-QTOF	splash10-0fr2-0000192000-dbfe316890501907db18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 40V, Negative-QTOF	splash10-0aor-9202420000-e05573710a8f58a421d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 10V, Positive-QTOF	splash10-0uxs-0000059000-3e978a72825660654a87	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 20V, Positive-QTOF	splash10-0udi-0000094000-2dfd35d7e9ce10554843	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 40V, Positive-QTOF	splash10-0fl1-8500193000-9281f959f7d6a0dfa98b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 10V, Negative-QTOF	splash10-0imi-0200219000-3319c9ecec161550e327	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 20V, Negative-QTOF	splash10-0ik9-2000395000-60d0b7e3401384f6ddb3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Natamycin 40V, Negative-QTOF	splash10-0udi-1000390000-a1a7a8f92824688e8cf0	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00826	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00826	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002337

KNApSAcK ID

Not Available

Chemspider ID

21242908

KEGG Compound ID

C08073

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Natamycin

METLIN ID

Not Available

PubChem Compound

5281099

PDB ID

Not Available

ChEBI ID

7488

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1274881

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Natamycin (HMDB0014964)

MOL for HMDB0014964 (Natamycin)

3D MOL for HMDB0014964 (Natamycin)

3D SDF for HMDB0014964 (Natamycin)

3D-SDF for HMDB0014964 (Natamycin)

PDB for HMDB0014964 (Natamycin)

3D PDB for HMDB0014964 (Natamycin)

SMILES for HMDB0014964 (Natamycin)

INCHI for HMDB0014964 (Natamycin)

Structure for HMDB0014964 (Natamycin)

3D Structure for HMDB0014964 (Natamycin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra