NP-MRD: Showing NP-Card for methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate (NP0144131)

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Record Information

Version

1.0

Created at

2022-09-01 23:01:26 UTC

Updated at

2022-09-01 23:01:27 UTC

NP-MRD ID

NP0144131

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Description

Fusarin A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. It was first documented in 2006 (PMID: 16908037). Based on a literature review a small amount of articles have been published on Fusarin A (PMID: 34296733) (PMID: 34195739) (PMID: 18041599).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022201012D          

 30 31  0  0  1  0            999 V2000
    4.1140   -8.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620   -7.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -7.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579   -6.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2649   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059   -5.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1608   -5.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -4.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -3.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -2.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5001   -8.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521   -9.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6931   -8.8671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4382   -9.6517    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  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 21 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    8.1227    3.1101   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7643    3.0647   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8918    2.0093   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6507    2.0923   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390    1.5816    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8849    0.2243   -1.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870    1.1717    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1472    0.8471    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8474    1.4872    2.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218    0.5148    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520    0.1294    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3145   -0.2688    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317   -0.5853   -0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616   -0.4745   -2.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4061   -0.8478   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855   -1.1560   -1.9250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4517   -0.8614    0.2878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7146   -0.3148   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0216    1.0059   -0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6416   -1.2006    0.0572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1508   -2.4664    0.5185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2907   -3.4410   -0.4604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7044   -2.8632    1.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4691   -3.3592    2.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5168   -2.3884    2.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817   -2.2354    0.8483 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6004    1.0502   -1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1469    0.0103   -1.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9344    1.2539   -1.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6272    0.3764   -2.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1280    3.1799   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7405    2.3145   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5794    4.0994   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3419    3.8101    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4154    3.0396    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -0.2178   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9993    0.9224   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -0.1895   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7262    1.0174   -1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8548    1.4843    1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843    0.6693    2.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2408    2.3508    2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291    0.4569    2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    0.1387   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555   -0.3468    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373    0.5685   -2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -0.5974   -2.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4692   -1.2118   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0307   -0.2618    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0004    1.1595   -0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -3.9406   -0.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4935   -3.6697    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1297   -1.9438    2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136   -4.3588    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5752   -3.3618    3.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -2.9971    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5755    0.1034   -2.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0096   -0.5186   -2.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9646    0.8346   -3.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 27  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 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  6
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 21 26  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
  2 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 17 49  1  1
 26 56  1  6
 24 54  1  0
 24 55  1  0
 23 52  1  0
 23 53  1  0
 22 51  1  0
 19 50  1  0
M  END


  Mrv1652309022201012D          

 30 31  0  0  1  0            999 V2000
    4.1140   -8.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620   -7.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -7.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579   -6.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2649   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059   -5.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1608   -5.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -4.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -3.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -2.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5001   -8.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521   -9.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6931   -8.8671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4382   -9.6517    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  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 21 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C(=C/C)\C=C(/C)\C=C(/C)\C=C\C=C(/C)C(=O)[C@@H]1C2OCC[C@@]2(O)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO6/c1-6-17(22(27)29-5)13-15(3)12-14(2)8-7-9-16(4)19(25)18-20-23(28,10-11-30-20)24-21(18)26/h6-9,12-13,18,20,28H,10-11H2,1-5H3,(H,24,26)/b8-7+,14-12+,15-13+,16-9+,17-6-/t18-,20?,23+/m1/s1

> <INCHI_KEY>
UOPODNWYGYPLAE-WFXIHSMNSA-N

> <FORMULA>
C23H29NO6

> <MOLECULAR_WEIGHT>
415.486

> <EXACT_MASS>
415.199487658

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.15911726876297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z,3E,5E,7E,9E)-11-[(3aS,6R)-3a,5-dihydroxy-2H,3H,3aH,6H,6aH-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.9456357790000003

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.836313222254615

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8684540227509507

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2939288327232927

> <JCHEM_POLAR_SURFACE_AREA>
105.42

> <JCHEM_REFRACTIVITY>
117.48639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z,3E,5E,7E,9E)-11-[(3aS,6R)-3a,5-dihydroxy-2H,3H,6H,6aH-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.679 -15.591   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.649 -14.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.143 -14.767   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.112 -13.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.588 -12.158   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.094 -11.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.558 -11.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.034  -9.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.540  -9.229   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.003  -8.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.479  -6.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.449  -5.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.924  -4.331   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.431  -4.011   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.075  -0.476   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       2.370   0.770   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.834   1.834   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.299  -1.722   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.667 -16.232   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.697 -17.376   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.160 -16.552   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.685 -18.017   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
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   26                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17   21                                                  
CONECT   27    3   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉NO₆

Average Mass

415.4860 Da

Monoisotopic Mass

415.19949 Da

IUPAC Name

methyl (2Z,3E,5E,7E,9E)-11-[(3aS,6R)-3a,5-dihydroxy-2H,3H,3aH,6H,6aH-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Traditional Name

methyl (2Z,3E,5E,7E,9E)-11-[(3aS,6R)-3a,5-dihydroxy-2H,3H,6H,6aH-furo[3,2-b]pyrrol-6-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@@H]1C2OCC[C@@]2(O)N=C1O

InChI Identifier

InChI=1S/C23H29NO6/c1-6-17(22(27)29-5)13-15(3)12-14(2)8-7-9-16(4)19(25)18-20-23(28,10-11-30-20)24-21(18)26/h6-9,12-13,18,20,28H,10-11H2,1-5H3,(H,24,26)/b8-7+,14-12+,15-13+,16-9+,17-6-/t18-,20?,23+/m1/s1

InChI Key

UOPODNWYGYPLAE-WFXIHSMNSA-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
Furopyrrole
Fatty acid ester
Pyrrolidone
2-pyrrolidone
Fatty acyl
1,3-dicarbonyl compound
Alpha-branched alpha,beta-unsaturated-ketone
Acryloyl-group
Enone
Oxolane
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Carboxamide group
Lactam
Ketone
Secondary carboxylic acid amide
Dialkyl ether
Carboxylic acid derivative
Alkanolamine
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Ether
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
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	2.76	ALOGPS
logP	3.95	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.42 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	117.49 m³·mol⁻¹	ChemAxon
Polarizability	45.16 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101837988

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang Q, Wang W, Lin Y, Lin Y, Tang Z, Wang J, Tao J, Tang W, Liu W: Correction: Characterization of a carboxyl methyltransferase in Fusarium graminearum provides insights into the biosynthesis of fusarin A. Org Biomol Chem. 2021 Aug 5;19(30):6718. doi: 10.1039/d1ob90103f. [PubMed:34296733 ]
Uhlig S, Jestoi M, Kristin Knutsen A, Heier BT: Multiple regression analysis as a tool for the identification of relations between semi-quantitative LC-MS data and cytotoxicity of extracts of the fungus Fusarium avenaceum (syn. F. arthrosporioides). Toxicon. 2006 Oct;48(5):567-79. doi: 10.1016/j.toxicon.2006.07.007. Epub 2006 Jul 7. [PubMed:16908037 ]
Yang Q, Wang W, Lin Y, Lin Y, Tang Z, Wang J, Tao J, Tang W, Liu W: Characterization of a carboxyl methyltransferase in Fusarium graminearum provides insights into the biosynthesis of fusarin A. Org Biomol Chem. 2021 Aug 5;19(30):6638-6643. doi: 10.1039/d1ob01010g. [PubMed:34195739 ]
Maragos CM, Busman M, Plattner RD: Development of monoclonal antibodies for the fusarin mycotoxins. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 Jan;25(1):105-14. doi: 10.1080/02652030701518098. [PubMed:18041599 ]
LOTUS database [Link]

Showing NP-Card for methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate (NP0144131)

MOL for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D MOL for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D SDF for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D-SDF for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

PDB for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D PDB for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

SMILES for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

INCHI for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

Structure for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D Structure for NP0144131 (methyl (2z,3e,5e,7e,9e)-11-[(3as,6r)-3a,5-dihydroxy-2h,3h,6h,6ah-furo[3,2-b]pyrrol-6-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)