NP-MRD: Showing NP-Card for Furanodictine A (NP0003891)

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Record Information

Version

2.0

Created at

2020-12-09 01:26:34 UTC

Updated at

2021-07-15 16:47:39 UTC

NP-MRD ID

NP0003891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Furanodictine A

Provided By

NPAtlas

Description

N-[(3R,3aR,6R,6aS)-2-hydroxy-6-[(3-methylbutanoyl)oxy]-hexahydrofuro[3,2-b]furan-3-yl]ethanimidic acid belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Furanodictine A is found in Dictyostelium discoideum. Furanodictine A was first documented in 2001 (PMID: 11597217). Based on a literature review very few articles have been published on N-[(3R,3aR,6R,6aS)-2-hydroxy-6-[(3-methylbutanoyl)oxy]-hexahydrofuro[3,2-b]furan-3-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117503D          

 41 42  0  0  0  0            999 V2000
    6.2147    1.6271   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.4696   -0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7509   -0.6547   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799    0.5942   -0.2100 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -0.5764   -0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5887   -0.6970    1.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0798   -1.8772    1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.6843    1.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.0879    0.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3694   -0.3806   -0.5662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4280   -0.6145    0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -0.0503    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.7128   -0.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -0.4039    1.1391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0339    0.2750    0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5920   -0.1052   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073    1.7629    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.7105   -1.1344 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4454   -1.5169   -1.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -0.3765   -0.8961 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2797    1.3045   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    2.3964   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0844    2.1165   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    1.5454    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -1.4787   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    0.1801    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -2.3230    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    1.1626    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    0.2883   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132   -1.5097    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251   -0.2275    2.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -0.0034    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.1535   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.0503   -0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1742    0.6196   -1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6798    2.3070    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840    2.0492    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.1938   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -2.1118   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -2.4159   -0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.3853   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  5  1  0  0  0  0
 20  9  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  6  0  0  0
  6 26  1  1  0  0  0
  7 27  1  0  0  0  0
  9 28  1  1  0  0  0
 10 29  1  6  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 32  1  1  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
 20 41  1  6  0  0  0
M  END

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    6.2147    1.6271   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.4696   -0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7509   -0.6547   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799    0.5942   -0.2100 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -0.5764   -0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5887   -0.6970    1.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0798   -1.8772    1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.6843    1.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.0879    0.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3694   -0.3806   -0.5662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4280   -0.6145    0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -0.0503    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.7128   -0.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -0.4039    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0339    0.2750    0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5920   -0.1052   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073    1.7629    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.7105   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454   -1.5169   -1.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -0.3765   -0.8961 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2797    1.3045   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    2.3964   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0844    2.1165   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    1.5454    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -1.4787   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    0.1801    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -2.3230    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    1.1626    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    0.2883   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132   -1.5097    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251   -0.2275    2.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -0.0034    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.1535   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.0503   -0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1742    0.6196   -1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6798    2.3070    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840    2.0492    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.1938   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -2.1118   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -2.4159   -0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.3853   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20  5  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  1
  7 27  1  0
  9 28  1  1
 10 29  1  6
 14 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  6
M  END


  Mrv1652306242117503D          

 41 42  0  0  0  0            999 V2000
    6.2147    1.6271   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.4696   -0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7509   -0.6547   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799    0.5942   -0.2100 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -0.5764   -0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5887   -0.6970    1.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0798   -1.8772    1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.6843    1.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.0879    0.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3694   -0.3806   -0.5662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4280   -0.6145    0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -0.0503    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.7128   -0.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -0.4039    1.1391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0339    0.2750    0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5920   -0.1052   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073    1.7629    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.7105   -1.1344 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4454   -1.5169   -1.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -0.3765   -0.8961 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2797    1.3045   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    2.3964   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0844    2.1165   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    1.5454    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -1.4787   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    0.1801    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -2.3230    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    1.1626    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    0.2883   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132   -1.5097    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251   -0.2275    2.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -0.0034    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.1535   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.0503   -0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1742    0.6196   -1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6798    2.3070    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840    2.0492    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.1938   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -2.1118   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -2.4159   -0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.3853   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  5  1  0  0  0  0
 20  9  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  6  0  0  0
  6 26  1  1  0  0  0
  7 27  1  0  0  0  0
  9 28  1  1  0  0  0
 10 29  1  6  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 32  1  1  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
 20 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0003891

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO6/c1-6(2)4-9(16)19-8-5-18-12-10(14-7(3)15)13(17)20-11(8)12/h6,8,10-13,17H,4-5H2,1-3H3,(H,14,15)/t8-,10-,11-,12-,13-/m1/s1

> <INCHI_KEY>
XACKKSAZFKSCJT-FLBHPLMVSA-N

> <FORMULA>
C13H21NO6

> <MOLECULAR_WEIGHT>
287.312

> <EXACT_MASS>
287.1368874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.346819306718523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,6R,6aR)-6-acetamido-5-hydroxy-hexahydrofuro[3,2-b]furan-3-yl 3-methylbutanoate

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-0.18562182066666624

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.454555012595847

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.656865396684665

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5713211259082276

> <JCHEM_POLAR_SURFACE_AREA>
94.09000000000002

> <JCHEM_REFRACTIVITY>
66.44260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,6R,6aR)-6-acetamido-5-hydroxy-hexahydrofuro[3,2-b]furan-3-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    6.2147    1.6271   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.4696   -0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7509   -0.6547   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799    0.5942   -0.2100 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -0.5764   -0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5887   -0.6970    1.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0798   -1.8772    1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.6843    1.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.0879    0.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3694   -0.3806   -0.5662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4280   -0.6145    0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -0.0503    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.7128   -0.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -0.4039    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0339    0.2750    0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5920   -0.1052   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073    1.7629    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.7105   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454   -1.5169   -1.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -0.3765   -0.8961 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2797    1.3045   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    2.3964   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0844    2.1165   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    1.5454    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -1.4787   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    0.1801    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -2.3230    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    1.1626    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    0.2883   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132   -1.5097    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251   -0.2275    2.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -0.0034    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.1535   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.0503   -0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1742    0.6196   -1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6798    2.3070    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840    2.0492    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.1938   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -2.1118   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -2.4159   -0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.3853   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20  5  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  1
  7 27  1  0
  9 28  1  1
 10 29  1  6
 14 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  6
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       6.215   1.627  -0.861  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.300   0.470  -0.679  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.751  -0.655  -0.963  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.980   0.594  -0.210  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.145  -0.576  -0.057  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.589  -0.697   1.338  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.080  -1.877   1.891  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.210  -0.684   1.225  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.896   0.088   0.123  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.369  -0.381  -0.566  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.428  -0.615   0.289  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.703  -0.050   0.142  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.871   0.713  -0.834  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.713  -0.404   1.139  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.034   0.275   0.856  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.592  -0.105  -0.488  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.807   1.763   0.895  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.136  -1.710  -1.134  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.445  -1.517  -1.481  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.917  -0.377  -0.896  0.00  0.00           C+0
HETATM   21  H   UNK     0       7.280   1.305  -0.807  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.074   2.396  -0.083  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.084   2.116  -1.849  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.623   1.545   0.022  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.708  -1.479  -0.355  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.930   0.180   1.960  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.745  -2.323   1.294  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.940   1.163   0.284  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.564   0.288  -1.398  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.913  -1.510   1.045  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.425  -0.228   2.180  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.783  -0.003   1.621  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.414  -1.153  -0.756  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.691   0.050  -0.452  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.174   0.620  -1.232  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.680   2.307   1.343  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.884   2.049   1.446  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.688   2.194  -0.135  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.513  -2.112  -1.908  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.130  -2.416  -0.253  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.070   0.385  -1.694  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6   20   25                                             
CONECT    6    5    7    8   26                                             
CONECT    7    6   27                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   20   28                                             
CONECT   10    9   11   18   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   30   31                                             
CONECT   15   14   16   17   32                                             
CONECT   16   15   33   34   35                                             
CONECT   17   15   36   37   38                                             
CONECT   18   10   19   39   40                                             
CONECT   19   18   20                                                       
CONECT   20   19    5    9   41                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   14                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   18                                                            
CONECT   41   20                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

RDKit          3D

41 42  0  0  0  0  0  0  0  0999 V2000
    6.2147    1.6271   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.4696   -0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7509   -0.6547   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799    0.5942   -0.2100 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -0.5764   -0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5887   -0.6970    1.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0798   -1.8772    1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.6843    1.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.0879    0.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3694   -0.3806   -0.5662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4280   -0.6145    0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -0.0503    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    0.7128   -0.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -0.4039    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0339    0.2750    0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5920   -0.1052   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073    1.7629    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.7105   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454   -1.5169   -1.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -0.3765   -0.8961 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2797    1.3045   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741    2.3964   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0844    2.1165   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    1.5454    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -1.4787   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    0.1801    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -2.3230    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    1.1626    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    0.2883   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132   -1.5097    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251   -0.2275    2.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -0.0034    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.1535   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.0503   -0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1742    0.6196   -1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6798    2.3070    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840    2.0492    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.1938   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -2.1118   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302   -2.4159   -0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.3853   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20  5  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  1
  7 27  1  0
  9 28  1  1
 10 29  1  6
 14 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
N-[(3R,3AR,6R,6as)-2-hydroxy-6-[(3-methylbutanoyl)oxy]-hexahydrofuro[3,2-b]furan-3-yl]ethanimidate	Generator

Chemical Formula

C₁₃H₂₁NO₆

Average Mass

287.3120 Da

Monoisotopic Mass

287.13689 Da

IUPAC Name

(3R,3aS,6R,6aR)-6-acetamido-5-hydroxy-hexahydrofuro[3,2-b]furan-3-yl 3-methylbutanoate

Traditional Name

(3R,3aS,6R,6aR)-6-acetamido-5-hydroxy-hexahydrofuro[3,2-b]furan-3-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@@H]1CO[C@@H]2[C@@H](NC(C)=O)C(O)O[C@H]12

InChI Identifier

InChI=1S/C13H21NO6/c1-6(2)4-9(16)19-8-5-18-12-10(14-7(3)15)13(17)20-11(8)12/h6,8,10-13,17H,4-5H2,1-3H3,(H,14,15)/t8-,10-,11-,12-,13?/m1/s1

InChI Key

XACKKSAZFKSCJT-FLBHPLMVSA-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
Dictyostelium discoideum	NPAtlas	11597217

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Fatty acid ester
Monosaccharide
Fatty acyl
Oxolane
Acetamide
Carboxamide group
Carboxylic acid ester
Hemiacetal
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.17	ALOGPS
logP	-0.19	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.44 m³·mol⁻¹	ChemAxon
Polarizability	29.35 Å³	ChemAxon
Number of Rings	2	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

NPA001916

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9589863

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11414976

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kikuchi H, Saito Y, Komiya J, Takaya Y, Honma S, Nakahata N, Ito A, Oshima Y: Furanodictine A and B: amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity. J Org Chem. 2001 Oct 19;66(21):6982-7. doi: 10.1021/jo015657x. [PubMed:11597217 ]

Showing NP-Card for Furanodictine A (NP0003891)

MOL for NP0003891 (Furanodictine A)

3D MOL for NP0003891 (Furanodictine A)

3D SDF for NP0003891 (Furanodictine A)

3D-SDF for NP0003891 (Furanodictine A)

PDB for NP0003891 (Furanodictine A)

3D PDB for NP0003891 (Furanodictine A)

SMILES for NP0003891 (Furanodictine A)

INCHI for NP0003891 (Furanodictine A)

Structure for NP0003891 (Furanodictine A)

3D Structure for NP0003891 (Furanodictine A)