NP-MRD: Showing NP-Card for (2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one (NP0200537)

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Record Information

Version

2.0

Created at

2022-09-04 19:24:04 UTC

Updated at

2022-09-04 19:24:04 UTC

NP-MRD ID

NP0200537

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one

Description

Fusarin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one is found in Fusarium verticillioides. (2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one was first documented in 2021 (PMID: 34296733). Based on a literature review a small amount of articles have been published on Fusarin (PMID: 34575814) (PMID: 34214671) (PMID: 34195739) (PMID: 34070447).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221242D          

 28 29  0  0  1  0            999 V2000
   -5.9701    2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208    0.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1563   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003    0.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8509   -0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6949    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -0.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -2.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0059    1.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    0.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -1.8060    0.0000 O   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
  3  5  1  0  0  0  0
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  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 16  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
   -6.5320    3.7249   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4595    2.6672   -0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9878    1.4753   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0756    0.5710   -1.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5985    1.3470   -1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019    0.3818   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4406   -0.7454   -2.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    0.5402   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    0.1101   -1.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067   -1.1617   -2.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8909   -0.3536   -1.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.4208   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3300   -0.9240   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.0409    0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -0.6640    1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5610   -1.5490    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7970   -1.8530   -1.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6678   -1.7514    1.0400 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5356   -1.4227    2.3871 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.5057    1.6508 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7144   -0.6823    1.4246 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0991    0.2936    0.4729 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5586   -0.4839    2.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230    0.9260    3.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9782    1.1515    3.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020   -1.9496    0.8480 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8105   -2.5518    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056   -3.8285    0.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283    3.5474    0.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1516    4.6784   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7059    3.9446   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4961    2.8310   -0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0769    0.9914   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0393   -0.4197   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1888    0.5814   -2.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057    2.1952   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9340   -1.2554   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.4409   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1226   -1.7708   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -1.4114   -2.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4003   -0.6890   -2.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -0.0740    0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -1.2291   -1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -1.5547    2.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5509    0.1930    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054   -0.4024    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739    0.4787    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6880    0.1349   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312   -0.5688    2.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2396   -1.2040    3.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9555    1.1390    4.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7861    2.0645    3.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8213   -4.2298   -0.2496 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
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 14 15  1  0
 14 16  1  0
 16 17  2  0
 18 16  1  6
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 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 27 28  1  0
 20 18  1  0
 27 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
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 20 50  1  6
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 28 57  1  0
M  END


  Mrv1652309042221242D          

 28 29  0  0  1  0            999 V2000
   -5.9701    2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208    0.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1563   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003    0.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8509   -0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6949    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -0.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -2.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0059    1.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    0.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -1.8060    0.0000 O   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
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  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 16 17  2  0  0  0  0
 18 16  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
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 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200537

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)/C=C(\C)/C=C(\C)/C=C/C=C(\C)C(=O)[C@]12O[C@H]1[C@@](O)(CCO)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO5/c1-6-14(2)12-16(4)13-15(3)8-7-9-17(5)18(25)22-19(28-22)21(27,10-11-24)23-20(22)26/h6-9,12-13,19,24,27H,10-11H2,1-5H3,(H,23,26)/b8-7+,14-6-,15-13+,16-12+,17-9+/t19-,21-,22-/m0/s1

> <INCHI_KEY>
RCJADKVBRBVIEX-YAMKEULKSA-N

> <FORMULA>
C22H29NO5

> <MOLECULAR_WEIGHT>
387.476

> <EXACT_MASS>
387.204573038

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.85131292639765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10Z)-1-[(1S,4S,5R)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one

> <JCHEM_LOGP>
3.7831981276666653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.748466250739444

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8651292440653364

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3338286392939716

> <JCHEM_POLAR_SURFACE_AREA>
102.65

> <JCHEM_REFRACTIVITY>
112.24609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E,10Z)-1-[(1S,4S,5R)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.144   3.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.771   2.587   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.865   1.341   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.492  -0.066   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.334   1.502   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.429   0.256   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.055  -1.151   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.897   0.417   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.992  -0.829   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.618  -2.236   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.460  -0.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.555  -1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.024  -1.753   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.118  -2.999   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.745  -4.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.413  -2.838   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.318  -4.083   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.039  -1.431   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.294  -0.661   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.039   0.109   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.504   0.585   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.878   1.992   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.838   1.355   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.171   0.585   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.505   1.355   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       3.409  -0.661   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       2.504  -1.907   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.980  -3.371   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   27                                             
CONECT   19   18   20                                                       
CONECT   20   19   18   21                                                  
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   21   27                                                       
CONECT   27   26   18   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₅

Average Mass

387.4760 Da

Monoisotopic Mass

387.20457 Da

IUPAC Name

(2E,4E,6E,8E,10Z)-1-[(1S,4S,5R)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one

Traditional Name

(2E,4E,6E,8E,10Z)-1-[(1S,4S,5R)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one

CAS Registry Number

Not Available

SMILES

C\C=C(\C)/C=C(\C)/C=C(\C)/C=C/C=C(\C)C(=O)[C@]12O[C@H]1[C@@](O)(CCO)N=C2O

InChI Identifier

InChI=1S/C22H29NO5/c1-6-14(2)12-16(4)13-15(3)8-7-9-17(5)18(25)22-19(28-22)21(27,10-11-24)23-20(22)26/h6-9,12-13,19,24,27H,10-11H2,1-5H3,(H,23,26)/b8-7+,14-6-,15-13+,16-12+,17-9+/t19-,21-,22-/m0/s1

InChI Key

RCJADKVBRBVIEX-YAMKEULKSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium verticillioides	LOTUS Database	35616633

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
Morpholine
Oxazinane
Pyrrolidone
2-pyrrolidone
Alpha-branched alpha,beta-unsaturated-ketone
Acryloyl-group
Enone
Pyrrolidine
Alpha,beta-unsaturated ketone
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Alkanolamine
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Alcohol
Organooxygen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
Organopnictogen compound
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	3.78	ChemAxon
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.65 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	112.25 m³·mol⁻¹	ChemAxon
Polarizability	42.85 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

C00002445

Chemspider ID

13085526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fusarin

METLIN ID

Not Available

PubChem Compound

15942871

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 ]
N D, Achar PN, Sreenivasa MY: Current Perspectives of Biocontrol Agents for Management of Fusarium verticillioides and Its Fumonisin in Cereals-A Review. J Fungi (Basel). 2021 Sep 18;7(9):776. doi: 10.3390/jof7090776. [PubMed:34575814 ]
Bachleitner S, Sulyok M, Sorensen JL, Strauss J, Studt L: The H4K20 methyltransferase Kmt5 is involved in secondary metabolism and stress response in phytopathogenic Fusarium species. Fungal Genet Biol. 2021 Oct;155:103602. doi: 10.1016/j.fgb.2021.103602. Epub 2021 Jun 30. [PubMed:34214671 ]
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 ]
Luo G, Zheng L, Wu Q, Chen S, Li J, Liu L: Fusarins G-L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227. Mar Drugs. 2021 May 25;19(6):305. doi: 10.3390/md19060305. [PubMed:34070447 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one (NP0200537)

MOL for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

3D MOL for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

3D SDF for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

3D-SDF for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

PDB for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

3D PDB for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

SMILES for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

INCHI for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

Structure for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)

3D Structure for NP0200537 ((2e,4e,6e,8e,10z)-1-[(1s,4s,5r)-2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2,6,8,10-tetramethyldodeca-2,4,6,8,10-pentaen-1-one)