NP-MRD: Showing NP-Card for methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate (NP0173099)

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Record Information

Version

2.0

Created at

2022-09-03 10:11:11 UTC

Updated at

2022-09-03 10:11:11 UTC

NP-MRD ID

NP0173099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Description

Fusarin F belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on Fusarin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212112D          

 31 32  0  0  1  0            999 V2000
    4.3859    7.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    8.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149    7.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149    6.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    6.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    6.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    5.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    5.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    5.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    4.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    4.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    3.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    2.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    3.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    1.5536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9070    2.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525    0.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1224   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337   -1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5294    8.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5294    8.9786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2438    7.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9583    8.1536    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 27 26  1  1  0  0  0
 22 27  1  0  0  0  0
 17 27  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -7.2863    0.2618    2.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6928    1.5809    1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5413    1.3806    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525    1.1572    0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5053    0.0020    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2150   -1.0004    1.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1901   -0.0521    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3866   -1.0988    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -2.3858    1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684   -0.9400   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787   -1.9152   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -1.7349   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -2.7324   -1.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -4.0711   -0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006   -2.7352   -1.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034   -3.9356   -1.8648 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9958   -1.5983   -2.1371 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8826   -2.0599   -3.1454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2983   -0.3774   -2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3811   -0.1382   -3.5272 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6019    0.5734   -1.6354 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    0.1690   -0.6405 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6833    1.1254   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0426    2.4556    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2862    2.9793   -1.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3381   -0.8894    0.2087 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9718   -1.2220   -0.9940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4628    3.1049    0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    3.3253    0.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927    3.8308    0.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5903    5.2137    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9192   -0.5774    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3528    0.3349    2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9508    0.2567    3.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4184    2.3524    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6648    1.8437    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305   -0.4635    2.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8626   -1.7017    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4805   -1.5587    2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700    0.8652   -0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245   -2.7097    0.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4657   -2.5436    2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736   -3.1761    0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    0.0229   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5641   -2.8826    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198   -0.7436   -1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -4.8935   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598   -4.0723    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -4.2215   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225   -1.4994   -3.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579    0.7800   -3.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149    1.2756   -1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3616    0.7382    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142    2.3039    0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8290    3.1855    0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7675    3.7870   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9711   -1.5894   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9967    5.8188    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1018    5.2686   -0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5344    5.5262    0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
 28 29  2  0
 28  3  1  0
  3  2  2  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 27  1  0
 27 26  1  0
 26 22  1  0
 22 23  1  1
 23 24  1  0
 24 25  1  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 19 17  1  0
 22 27  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
  2 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 18 50  1  0
 27 57  1  1
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 20 51  1  0
M  END


  Mrv1652309032212112D          

 31 32  0  0  1  0            999 V2000
    4.3859    7.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    8.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149    7.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149    6.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    6.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    6.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    5.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    5.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    5.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    4.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    4.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    3.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    2.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    3.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    1.5536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9070    2.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525    0.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1224   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337   -1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5294    8.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5294    8.9786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2438    7.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9583    8.1536    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 27 26  1  1  0  0  0
 22 27  1  0  0  0  0
 17 27  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173099

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C(=C\C)\C=C(/C)\C=C(/C)\C=C\C=C(/C)C(=O)[C@]1(O)[C@@H]2O[C@]2(CCO)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO7/c1-6-17(19(27)30-5)13-15(3)12-14(2)8-7-9-16(4)18(26)23(29)20-22(31-20,10-11-25)24-21(23)28/h6-9,12-13,20,25,29H,10-11H2,1-5H3,(H,24,28)/b8-7+,14-12+,15-13+,16-9+,17-6+/t20-,22+,23+/m1/s1

> <INCHI_KEY>
AIBXKQALOBROCW-ZKSHOXQKSA-N

> <FORMULA>
C23H29NO7

> <MOLECULAR_WEIGHT>
431.485

> <EXACT_MASS>
431.194402278

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.4958972637548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,3E,5E,7E,9E)-11-[(1S,4S,5S)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
3.3541181159999995

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.296051851285831

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9188848270214662

> <JCHEM_PKA_STRONGEST_BASIC>
-2.433090051688389

> <JCHEM_POLAR_SURFACE_AREA>
128.95000000000002

> <JCHEM_REFRACTIVITY>
118.7324

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,3E,5E,7E,9E)-11-[(1S,4S,5S)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.187  14.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.521  15.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.854  14.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.854  12.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.521  12.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.187  12.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.521  10.600   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.187   9.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.853  10.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.187   8.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.853   7.520   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.853   5.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.520   5.210   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.186   5.980   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.520   3.670   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.853   2.900   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.186   2.900   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.560   4.307   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.091   1.654   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.631   1.654   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       4.186   0.408   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.721   0.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.095  -0.523   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.563  -0.684   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.063  -2.090   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.388   1.654   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.721   2.424   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.188  15.220   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.188  16.760   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.522  14.450   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.855  15.220   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   27                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   26   27                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27                                                       
CONECT   27   26   22   17                                                  
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉NO₇

Average Mass

431.4850 Da

Monoisotopic Mass

431.19440 Da

IUPAC Name

methyl (2E,3E,5E,7E,9E)-11-[(1S,4S,5S)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Traditional Name

methyl (2E,3E,5E,7E,9E)-11-[(1S,4S,5S)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C(=C\C)\C=C(/C)\C=C(/C)\C=C\C=C(/C)C(=O)[C@]1(O)[C@@H]2O[C@]2(CCO)N=C1O

InChI Identifier

InChI=1S/C23H29NO7/c1-6-17(19(27)30-5)13-15(3)12-14(2)8-7-9-16(4)18(26)23(29)20-22(31-20,10-11-25)24-21(23)28/h6-9,12-13,20,25,29H,10-11H2,1-5H3,(H,24,28)/b8-7+,14-12+,15-13+,16-9+,17-6+/t20-,22+,23+/m1/s1

InChI Key

AIBXKQALOBROCW-ZKSHOXQKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Farsesane sesquiterpenoid
Fatty acid ester
1,3-oxazinane
Oxazinane
Pyrrolidone
2-pyrrolidone
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Acryloyl-group
Alpha-hydroxy ketone
Enone
Pyrrolidine
Tertiary alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Ketone
Lactam
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Oxirane
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Primary alcohol
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organonitrogen compound
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	2.4	ALOGPS
logP	3.35	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	1.92	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.95 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.73 m³·mol⁻¹	ChemAxon
Polarizability	46.5 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439704

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101580234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate (NP0173099)

MOL for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D MOL for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D SDF for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D-SDF for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

PDB for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D PDB for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

SMILES for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

INCHI for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

Structure for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D Structure for NP0173099 (methyl (2e,3e,5e,7e,9e)-11-[(1s,4s,5s)-3,4-dihydroxy-1-(2-hydroxyethyl)-6-oxa-2-azabicyclo[3.1.0]hex-2-en-4-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)