NP-MRD: Showing NP-Card for fostriecin (NP0155504)

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Record Information

Version

2.0

Created at

2022-09-02 12:34:29 UTC

Updated at

2022-09-02 12:34:29 UTC

NP-MRD ID

NP0155504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fostriecin

Description

Fostriecin belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. fostriecin is found in Streptomyces pulveraceus. fostriecin was first documented in 2018 (PMID: 30457629). Based on a literature review a small amount of articles have been published on fostriecin (PMID: 33890790) (PMID: 33184589) (PMID: 31584287) (PMID: 31433167).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214342D          

 29 29  0  0  1  0            999 V2000
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6039    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
M  END

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
   -2.8993   -1.0949    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7040   -0.7377    1.2350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1222   -1.9457    0.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845   -0.1270   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    0.7612   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8312    1.3700   -1.2495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3297    1.2972   -1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    1.9078   -2.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0520    1.9367   -3.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273    1.3278   -3.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9872    1.3221   -4.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372    0.7652   -2.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.2637    1.9078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2492    0.8142    1.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441   -0.1632    0.5710 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6918   -1.0974   -0.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337    0.5160   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3861   -0.1856   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889   -1.5833   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5050   -2.3114   -0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6222   -1.7814   -1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6469   -2.5660   -1.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7988   -2.0217   -2.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6522   -0.6770   -2.7846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    1.3153    2.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8799    1.5256    3.8909 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3056    1.9062    4.2235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.2261    4.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9318    2.8904    4.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -1.7927    1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4817   -1.6723    2.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -0.2168    2.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2753   -2.6419    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8755   -0.4472   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555    1.0760    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5534    2.4484   -1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7800    1.8157   -0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6361    0.2179   -1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7649    2.3618   -2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4358    2.4039   -4.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930   -0.1391    2.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7541    1.7039    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701    1.3156    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7113   -0.7640    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5508   -0.7842   -1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    1.5702   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1844    0.3169   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -2.0952    0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5281   -3.3874   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6928   -0.7684   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6077   -3.5958   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9211   -2.5740   -3.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7232   -2.1739   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9599   -0.1262   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803    0.3995    5.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    3.6959    3.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 13 25  1  0
 25 26  1  0
 26 28  1  0
 26 29  1  0
 26 27  2  0
 12  6  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  1
 14 42  1  0
 14 43  1  0
 15 44  1  1
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 28 55  1  0
 29 56  1  0
M  END


  Mrv1652309022214342D          

 29 29  0  0  1  0            999 V2000
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6039    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@](O)(\C=C\[C@@H]1CC=CC(=O)O1)[C@@H](C[C@@H](O)\C=C/C=C\C=C\CO)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H27O9P/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26)/b3-2-,6-4+,8-5-,12-11+/t15-,16-,17+,19+/m0/s1

> <INCHI_KEY>
ZMQRJWIYMXZORG-GZIFKOAOSA-N

> <FORMULA>
C19H27O9P

> <MOLECULAR_WEIGHT>
430.39

> <EXACT_MASS>
430.139269447

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.43611778069289

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]trideca-1,7,9,11-tetraen-4-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
0.6297700949999996

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.563161151054079

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5337105782613363

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2712147315117948

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
111.50329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]trideca-1,7,9,11-tetraen-4-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.207   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.127   6.160   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  14.630   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0       4.001  10.010   0.000  0.00  0.00           P+0
HETATM   27  O   UNK     0       5.541  10.010   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.461  10.010   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   13                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6                                                       
CONECT   13    2   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   13   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₇O₉P

Average Mass

430.3900 Da

Monoisotopic Mass

430.13927 Da

IUPAC Name

{[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]trideca-1,7,9,11-tetraen-4-yl]oxy}phosphonic acid

Traditional Name

[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]trideca-1,7,9,11-tetraen-4-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

C[C@@](O)(\C=C\[C@@H]1CC=CC(=O)O1)[C@@H](C[C@@H](O)\C=C/C=C\C=C\CO)OP(O)(O)=O

InChI Identifier

InChI=1S/C19H27O9P/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26)/b3-2-,6-4+,8-5-,12-11+/t15-,16-,17+,19+/m0/s1

InChI Key

ZMQRJWIYMXZORG-GZIFKOAOSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces pulveraceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.3	ALOGPS
logP	0.63	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	111.5 m³·mol⁻¹	ChemAxon
Polarizability	42.44 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018551

Chemspider ID

4940932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fostriecin

METLIN ID

Not Available

PubChem Compound

6436285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Umemiya S, Terada M: Catalytic Enantioselective Allylation of Acetylenic Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis: Formal Synthesis of Fostriecin. Org Lett. 2021 May 7;23(9):3767-3771. doi: 10.1021/acs.orglett.1c01166. Epub 2021 Apr 23. [PubMed:33890790 ]
Dong G, Li B, O'Doherty G: Total and Formal Syntheses of Fostriecin. Org Chem Front. 2020 Nov 21;7(22):3608-3615. doi: 10.1039/d0qo01121e. Epub 2020 Oct 12. [PubMed:33184589 ]
Gao D, Li B, O'Doherty GA: Synthesis of Dehydro-Dephospho-Fostriecin and Formal Total Synthesis of Fostriecin. Org Lett. 2019 Oct 18;21(20):8334-8338. doi: 10.1021/acs.orglett.9b03120. Epub 2019 Oct 4. [PubMed:31584287 ]
Della-Felice F, Sarotti AM, Krische MJ, Pilli RA: Total Synthesis and Structural Validation of Phosdiecin A via Asymmetric Alcohol-Mediated Carbonyl Reductive Coupling. J Am Chem Soc. 2019 Sep 4;141(35):13778-13782. doi: 10.1021/jacs.9b07512. Epub 2019 Aug 21. [PubMed:31433167 ]
Xie X, Cane DE: pH-Rate profiles establish that polyketide synthase dehydratase domains utilize a single-base mechanism. Org Biomol Chem. 2018 Dec 5;16(47):9165-9170. doi: 10.1039/c8ob02637h. [PubMed:30457629 ]
LOTUS database [Link]

Showing NP-Card for fostriecin (NP0155504)

MOL for NP0155504 (fostriecin)

3D MOL for NP0155504 (fostriecin)

3D SDF for NP0155504 (fostriecin)

3D-SDF for NP0155504 (fostriecin)

PDB for NP0155504 (fostriecin)

3D PDB for NP0155504 (fostriecin)

SMILES for NP0155504 (fostriecin)

INCHI for NP0155504 (fostriecin)

Structure for NP0155504 (fostriecin)

3D Structure for NP0155504 (fostriecin)