NP-MRD: Showing NP-Card for methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate (NP0275839)

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Record Information

Version

1.0

Created at

2022-09-08 23:43:00 UTC

Updated at

2022-09-08 23:43:01 UTC

NP-MRD ID

NP0275839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate

Description

3-Methoxy-4-chloro-5-(2-(2,5-dihydroxy-3-(3-methyl-2-butenyl)-3,4-epoxycyclohexane-1-ylidene)ethenyl)-5,7'-dimethyl-5'-hydroxy-4',8-dioxospiro[bicyclo[2.2.2]Octane-7,2'-[4H][1,3]benzodioxin]-2-ene-1-carboxylic acid methyl ester belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate is found in Pestalotiopsis fici. Based on a literature review very few articles have been published on 3-Methoxy-4-chloro-5-(2-(2,5-dihydroxy-3-(3-methyl-2-butenyl)-3,4-epoxycyclohexane-1-ylidene)ethenyl)-5,7'-dimethyl-5'-hydroxy-4',8-dioxospiro[bicyclo[2.2.2]Octane-7,2'-[4H][1,3]benzodioxin]-2-ene-1-carboxylic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092201432D          

 45 50  0  0  0  0            999 V2000
    0.7094   -1.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -1.3251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871   -0.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968   -0.3868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453    0.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9158    0.3834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838   -0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799    1.9440    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9716    1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395    2.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    1.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    2.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327    1.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425    1.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104    2.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4842    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648    0.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551    0.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6267    0.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233    0.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8269    1.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001    1.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6893    2.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6779    4.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1520    5.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396    5.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386    5.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    2.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072    2.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9879    0.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
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  5 14  1  0  0  0  0
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 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 37 43  1  0  0  0  0
 31 43  1  0  0  0  0
 43 44  1  0  0  0  0
 27 45  1  0  0  0  0
  5 45  1  0  0  0  0
M  END

     RDKit          3D

 80 85  0  0  0  0  0  0  0  0999 V2000
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    4.8820   -1.1286   -2.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8983   -1.4730   -1.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -2.6068   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929   -0.5904   -1.4397 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0300   -0.1856   -2.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596    0.5677   -2.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3851   -1.2540   -1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -0.4182    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2222   -0.6548    1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.9241    1.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8399   -2.3174    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3298   -2.4567    1.1152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4914   -2.6150   -0.2621 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  9 50  1  0
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  6 49  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
M  END


  Mrv1652309092201432D          

 45 50  0  0  0  0            999 V2000
    0.7094   -1.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -1.3251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871   -0.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968   -0.3868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453    0.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9158    0.3834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838   -0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799    1.9440    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9716    1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395    2.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    1.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    2.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327    1.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425    1.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104    2.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4842    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648    0.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551    0.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6267    0.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233    0.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    0.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    1.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4179    1.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    1.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8269    1.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001    1.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6893    2.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    3.6265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9161    3.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903    3.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    4.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1520    5.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396    5.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386    5.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    2.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072    2.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9879    0.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 37 43  1  0  0  0  0
 31 43  1  0  0  0  0
 43 44  1  0  0  0  0
 27 45  1  0  0  0  0
  5 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0275839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CC(C)(C=C=C3CC(O)C4OC4(CC=C(C)C)C3O)C(Cl)(C(OC)=C1)C(=O)C21OC(=O)C2=C(O)C=C(C)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C33H35ClO11/c1-16(2)7-10-31-24(37)18(13-20(36)25(31)44-31)8-9-29(4)15-30(28(40)42-6)14-22(41-5)32(29,34)27(39)33(30)43-21-12-17(3)11-19(35)23(21)26(38)45-33/h7,9,11-12,14,20,24-25,35-37H,10,13,15H2,1-6H3

> <INCHI_KEY>
WNDQDJWJVKECHL-UHFFFAOYSA-N

> <FORMULA>
C33H35ClO11

> <MOLECULAR_WEIGHT>
643.08

> <EXACT_MASS>
642.1867896

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
63.92112109591804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxo-4H-spiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate

> <JCHEM_LOGP>
4.843051916666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.026482940196026

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.793947645953294

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2339680909828665

> <JCHEM_POLAR_SURFACE_AREA>
161.35

> <JCHEM_REFRACTIVITY>
162.27290000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.324  -2.769   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.836  -2.474   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.336  -1.017   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.847  -0.722   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.325   0.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.813  -0.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.163   0.768   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.710   0.716   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.210  -0.741   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.302   2.467   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -0.709   3.629   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.814   2.762   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.314   4.219   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.825   1.601   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.325   3.057   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.837   3.352   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.337   4.809   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.848   2.191   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.359   2.486   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.859   3.943   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.371   1.325   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.870  -0.132   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.882  -1.293   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.359  -0.427   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.348   0.735   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.836   0.439   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.170   1.862   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.790   0.369   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.274   1.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.460   2.306   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.647   3.288   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.090   2.751   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.277   3.732   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.720   3.196   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.020   5.251   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.763   6.769   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.577   5.788   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.595   6.974   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.132   8.418   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.150   9.604   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.687  11.048   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.632   9.348   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.390   4.806   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.947   5.343   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.844   1.087   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14   45                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12   27                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15   26                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   14                                                       
CONECT   27   10   28   29   45                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   43                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35   37                                                       
CONECT   37   36   35   38   43                                             
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   37   31   44                                                  
CONECT   44   43                                                            
CONECT   45   27    5                                                       
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
3-Methoxy-4-chloro-5-(2-(2,5-dihydroxy-3-(3-methyl-2-butenyl)-3,4-epoxycyclohexane-1-ylidene)ethenyl)-5,7'-dimethyl-5'-hydroxy-4',8-dioxospiro[bicyclo[2.2.2]octane-7,2'-[4H][1,3]benzodioxin]-2-ene-1-carboxylate methyl ester	Generator

Chemical Formula

C₃₃H₃₅ClO₁₁

Average Mass

643.0800 Da

Monoisotopic Mass

642.18679 Da

IUPAC Name

methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxo-4H-spiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C12CC(C)(C=C=C3CC(O)C4OC4(CC=C(C)C)C3O)C(Cl)(C(OC)=C1)C(=O)C21OC(=O)C2=C(O)C=C(C)C=C2O1

InChI Identifier

InChI=1S/C33H35ClO11/c1-16(2)7-10-31-24(37)18(13-20(36)25(31)44-31)8-9-29(4)15-30(28(40)42-6)14-22(41-5)32(29,34)27(39)33(30)43-21-12-17(3)11-19(35)23(21)26(38)45-33/h7,9,11-12,14,20,24-25,35-37H,10,13,15H2,1-6H3

InChI Key

WNDQDJWJVKECHL-UHFFFAOYSA-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
Pestalotiopsis fici	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Cyclohexenone
Dicarboxylic acid or derivatives
Benzenoid
Alpha-haloketone
Cyclic alcohol
Alpha-chloroketone
Methyl ester
Vinylogous acid
Lactone
Secondary alcohol
Ketone
Carboxylic acid ester
Ether
Dialkyl ether
Acetal
Oxirane
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alkyl halide
Alkyl chloride
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.84	ChemAxon
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	161.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	162.27 m³·mol⁻¹	ChemAxon
Polarizability	63.92 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74950991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate (NP0275839)

MOL for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

3D MOL for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

3D SDF for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

3D-SDF for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

PDB for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

3D PDB for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

SMILES for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

INCHI for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

Structure for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)

3D Structure for NP0275839 (methyl 4'-chloro-8'-{2-[2,5-dihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-ylidene]ethenyl}-5-hydroxy-5'-methoxy-7,8'-dimethyl-3',4-dioxospiro[1,3-benzodioxine-2,2'-bicyclo[2.2.2]octan]-5'-ene-1'-carboxylate)