NP-MRD: Showing NP-Card for Open-Chain Fusarin C (NP0010785)

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Record Information

Version

2.0

Created at

2021-01-05 20:37:47 UTC

Updated at

2021-07-15 17:07:04 UTC

NP-MRD ID

NP0010785

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Open-Chain Fusarin C

Provided By

NPAtlas

Description

Open-Chain Fusarin C belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Open-Chain Fusarin C is found in Fusarium. Open-Chain Fusarin C was first documented in 2012 (PMID: 22540270). Based on a literature review very few articles have been published on Open-Chain Fusarin C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107413D          

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  Mrv1652306242107413D          

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   -9.0517   -0.7056   -0.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8025   -1.6799    1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9382   -2.0137    1.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0122    1.9547   -3.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4589    1.1837   -2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5718    0.4664   -3.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3343    0.3264   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8264   -0.0978   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4867   -1.6687    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8819   -2.8411    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373   -3.0461    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641    0.2364   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123   -3.0185    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -2.8356    1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -2.0613    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852   -1.7097    1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    0.4311   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -1.1342    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.9142   -0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852    0.6521   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884    1.9659   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    1.7333   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3368    0.1091   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6415    1.1981    2.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1449    2.9417   -0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3236    2.7662    1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0641    0.5525   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2367    0.2207    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4633    0.4564   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0720   -3.0725    2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8495   -1.5448    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6813   -1.5209    2.9523 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
  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  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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
 22 17  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
  4 36  1  0  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 10 44  1  0  0  0  0
 11 45  1  0  0  0  0
 12 46  1  0  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
 14 49  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 22 52  1  1  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
 27 57  1  0  0  0  0
 31 58  1  0  0  0  0
 31 59  1  0  0  0  0
 31 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010785

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO7/c1-6-17(21(28)30-5)13-15(3)12-14(2)8-7-9-16(4)19(27)23(22(24)29)20(31-23)18(26)10-11-25/h6-9,12-13,20,25H,10-11H2,1-5H3,(H2,24,29)/b8-7+,14-12+,15-13+,16-9+,17-6+/t20-,23-/m0/s1

> <INCHI_KEY>
NPNHTIINNIMBKL-DFBPGSKZSA-N

> <FORMULA>
C23H29NO7

> <MOLECULAR_WEIGHT>
431.485

> <EXACT_MASS>
431.194402278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.14549211498212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,3E,7E,9E)-11-[(2R,3R)-2-carbamoyl-3-(3-hydroxypropanoyl)oxiran-2-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.411641468333334

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.4663545558384

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.269516354799947

> <JCHEM_PKA_STRONGEST_BASIC>
-2.442970481876368

> <JCHEM_POLAR_SURFACE_AREA>
136.29

> <JCHEM_REFRACTIVITY>
119.51379999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,3E,7E,9E)-11-[(2R,3R)-2-carbamoyl-3-(3-hydroxypropanoyl)oxiran-2-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 60  0  0  0  0  0  0  0  0999 V2000
   -6.4858    0.9496   -2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2481    0.2269   -1.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7551   -0.5597   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571   -0.6838   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787   -1.3452   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0511   -2.2948    0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0819   -0.8936   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9019   -0.9634    0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2965   -2.5548    1.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5953   -1.0535    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -0.2710    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7558   -0.3737    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7769    0.3425    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296    1.3038   -0.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0314    0.2018    0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0708   -0.6784    1.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    0.9244    0.5547 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4816    1.7416   -0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3515    1.1276   -1.9824 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    2.9344   -0.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4089    0.0941    0.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2365    1.2071    1.6765 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3199    2.2096    1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2478    3.1145    2.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4224    2.2689    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8457    0.9748   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9278    1.2748   -0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8007   -1.0102   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0517   -0.7056   -0.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8025   -1.6799    1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9382   -2.0137    1.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0122    1.9547   -3.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4589    1.1837   -2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5718    0.4664   -3.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3343    0.3264   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8264   -0.0978   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4867   -1.6687    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8819   -2.8411    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373   -3.0461    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641    0.2364   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123   -3.0185    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -2.8356    1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -2.0613    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852   -1.7097    1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    0.4311   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -1.1342    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.9142   -0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852    0.6521   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884    1.9659   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    1.7333   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3368    0.1091   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6415    1.1981    2.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1449    2.9417   -0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3236    2.7662    1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0641    0.5525   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2367    0.2207    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4633    0.4564   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0720   -3.0725    2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8495   -1.5448    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6813   -1.5209    2.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
 17 15  1  1
 17 18  1  0
 18 19  1  0
 18 20  2  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
  3 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 22 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  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
 19 50  1  0
 19 51  1  0
 22 52  1  1
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.486   0.950  -2.957  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.248   0.227  -1.937  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.755  -0.560  -0.928  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.357  -0.684  -0.881  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.379  -1.345  -0.208  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.051  -2.295   0.807  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.082  -0.894  -0.119  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.902  -0.963   0.254  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.297  -2.555   1.099  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.595  -1.054   0.679  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.389  -0.271   0.158  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.756  -0.374   0.645  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.777   0.343   0.209  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.430   1.304  -0.869  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.031   0.202   0.834  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.071  -0.678   1.798  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.278   0.924   0.555  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.482   1.742  -0.686  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.351   1.128  -1.982  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.772   2.934  -0.561  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.409   0.094   0.909  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.237   1.207   1.677  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.320   2.210   1.561  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.248   3.115   2.428  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.422   2.269   0.601  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.846   0.975  -0.027  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.928   1.275  -0.877  0.00  0.00           O+0
HETATM   28  C   UNK     0      -7.801  -1.010  -0.010  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.052  -0.706  -0.336  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.803  -1.680   1.156  0.00  0.00           O+0
HETATM   31  C   UNK     0      -8.938  -2.014   1.949  0.00  0.00           C+0
HETATM   32  H   UNK     0      -7.012   1.955  -3.101  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.459   1.184  -2.662  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.572   0.466  -3.982  0.00  0.00           H+0
HETATM   35  H   UNK     0      -8.334   0.326  -1.974  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.826  -0.098  -1.703  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.487  -1.669   1.610  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.882  -2.841   0.261  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.437  -3.046   1.198  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.964   0.236  -0.707  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.712  -3.018   0.246  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.232  -2.836   1.172  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.655  -2.061   1.912  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.185  -1.710   1.469  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.151   0.431  -0.607  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.940  -1.134   1.433  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.515   1.914  -0.622  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.085   0.652  -1.770  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.188   1.966  -1.187  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.271   1.733  -2.814  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.337   0.109  -2.060  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.641   1.198   2.650  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.145   2.942  -0.252  0.00  0.00           H+0
HETATM   54  H   UNK     0       9.324   2.766   1.029  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.064   0.553  -0.728  0.00  0.00           H+0
HETATM   56  H   UNK     0       9.237   0.221   0.686  0.00  0.00           H+0
HETATM   57  H   UNK     0      10.463   0.456  -1.137  0.00  0.00           H+0
HETATM   58  H   UNK     0      -9.072  -3.072   2.145  0.00  0.00           H+0
HETATM   59  H   UNK     0      -9.850  -1.545   1.604  0.00  0.00           H+0
HETATM   60  H   UNK     0      -8.681  -1.521   2.952  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   35                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   37   38   39                                             
CONECT    7    5    8   40                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   41   42   43                                             
CONECT   10    8   11   44                                                  
CONECT   11   10   12   45                                                  
CONECT   12   11   13   46                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   47   48   49                                             
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21   22                                             
CONECT   18   17   19   20                                                  
CONECT   19   18   50   51                                                  
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   17   52                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   53   54                                             
CONECT   26   25   27   55   56                                             
CONECT   27   26   57                                                       
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   58   59   60                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   22                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   31                                                            
CONECT   59   31                                                            
CONECT   60   31                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  120    0
END

RDKit          3D

60 60  0  0  0  0  0  0  0  0999 V2000
   -6.4858    0.9496   -2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2481    0.2269   -1.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7551   -0.5597   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571   -0.6838   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787   -1.3452   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0511   -2.2948    0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0819   -0.8936   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9019   -0.9634    0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2965   -2.5548    1.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5953   -1.0535    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -0.2710    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7558   -0.3737    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7769    0.3425    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296    1.3038   -0.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0314    0.2018    0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0708   -0.6784    1.7976 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    0.9244    0.5547 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4816    1.7416   -0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3515    1.1276   -1.9824 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    2.9344   -0.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4089    0.0941    0.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2365    1.2071    1.6765 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3199    2.2096    1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2478    3.1145    2.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4224    2.2689    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8457    0.9748   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9278    1.2748   -0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8007   -1.0102   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0517   -0.7056   -0.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8025   -1.6799    1.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9382   -2.0137    1.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0122    1.9547   -3.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4589    1.1837   -2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5718    0.4664   -3.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3343    0.3264   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8264   -0.0978   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4867   -1.6687    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8819   -2.8411    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373   -3.0461    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641    0.2364   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123   -3.0185    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -2.8356    1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -2.0613    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852   -1.7097    1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    0.4311   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -1.1342    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.9142   -0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852    0.6521   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884    1.9659   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    1.7333   -2.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3368    0.1091   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6415    1.1981    2.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1449    2.9417   -0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3236    2.7662    1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0641    0.5525   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2367    0.2207    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4633    0.4564   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0720   -3.0725    2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8495   -1.5448    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6813   -1.5209    2.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
 17 15  1  1
 17 18  1  0
 18 19  1  0
 18 20  2  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
  3 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 22 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  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
 19 50  1  0
 19 51  1  0
 22 52  1  1
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S,3R)-2-[(2E,4E,6E,8E,10E)-10-Ethylidene-11-methoxy-2,6,8-trimethyl-11-oxoundeca-2,4,6,8-tetraenoyl]-3-(3-hydroxypropanoyl)oxirane-2-carboximidate	Generator

Chemical Formula

C₂₃H₂₉NO₇

Average Mass

431.4850 Da

Monoisotopic Mass

431.19440 Da

IUPAC Name

methyl (2E,3E,7E,9E)-11-[(2R,3R)-2-carbamoyl-3-(3-hydroxypropanoyl)oxiran-2-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Traditional Name

methyl (2E,3E,7E,9E)-11-[(2R,3R)-2-carbamoyl-3-(3-hydroxypropanoyl)oxiran-2-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]1C(=O)CCO)C(N)=O

InChI Identifier

InChI=1S/C23H29NO7/c1-6-17(21(28)30-5)13-15(3)12-14(2)8-7-9-16(4)19(27)23(22(24)29)20(31-23)18(26)10-11-25/h6-9,12-13,20,25H,10-11H2,1-5H3,(H2,24,29)/b8-7+,14-12+,15-13+,16-9+,17-6+/t20-,23-/m0/s1

InChI Key

NPNHTIINNIMBKL-DFBPGSKZSA-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
Fusarium	NPAtlas	22540270

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
Beta-hydroxy ketone
Fatty amide
Monosaccharide
Oxirane carboxylic acid or derivatives
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
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	2.18	ALOGPS
logP	2.41	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.27	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.29 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	119.51 m³·mol⁻¹	ChemAxon
Polarizability	48.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004052

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101580233

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kleigrewe K, Aydin F, Hogrefe K, Piecuch P, Bergander K, Wurthwein EU, Humpf HU: Structure elucidation of new fusarins revealing insights in the rearrangement mechanisms of the Fusarium mycotoxin fusarin C. J Agric Food Chem. 2012 May 30;60(21):5497-505. doi: 10.1021/jf3009469. Epub 2012 May 21. [PubMed:22540270 ]

Showing NP-Card for Open-Chain Fusarin C (NP0010785)

MOL for NP0010785 (Open-Chain Fusarin C)

3D MOL for NP0010785 (Open-Chain Fusarin C)

3D SDF for NP0010785 (Open-Chain Fusarin C)

3D-SDF for NP0010785 (Open-Chain Fusarin C)

PDB for NP0010785 (Open-Chain Fusarin C)

3D PDB for NP0010785 (Open-Chain Fusarin C)

SMILES for NP0010785 (Open-Chain Fusarin C)

INCHI for NP0010785 (Open-Chain Fusarin C)

Structure for NP0010785 (Open-Chain Fusarin C)

3D Structure for NP0010785 (Open-Chain Fusarin C)