NP-MRD: Showing NP-Card for methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate (NP0327586)

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Record Information

Version

2.0

Created at

2022-09-12 10:17:48 UTC

Updated at

2022-09-12 10:17:48 UTC

NP-MRD ID

NP0327586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate

Description

Methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]Dec-4-ene-1-carboxylate belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate is found in Pestalotiopsis fici. Methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]Dec-4-ene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518552D          

 44 49  0  0  0  0            999 V2000
    5.1000    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170    1.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289    1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459    2.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5237    0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077   -1.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6297   -0.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3229   -1.0086    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9102    0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720   -0.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846    0.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0827    0.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251    1.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379    2.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473    3.8030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5185    3.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2976    3.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057    2.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615    2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2037    1.2178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2293   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7441    2.0946    0.0000 O   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 21 22  1  0  0  0  0
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 22 23  1  0  0  0  0
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 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
 15 41  1  0  0  0  0
  9 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
  5 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END

     RDKit          3D

 77 82  0  0  0  0  0  0  0  0999 V2000
    6.8977    2.4763    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1528    1.2659    0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0908    0.9796    1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444    1.8264    2.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627   -0.2784    1.1706 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2489   -1.5138    1.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -2.6757    1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742   -3.7761    1.7390 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -2.4167    0.8927 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0056   -3.9153    0.7585 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2006   -1.3972    1.8097 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6890   -2.0724    2.8927 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9061    0.5704    0.3729 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.7683   -1.5315   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1830   -2.1004   -2.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3450   -2.8176   -2.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1647   -2.4631   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8467   -0.4620   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7120   -1.4283    2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2799    0.3960    3.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8728   -0.9474   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7517   -0.6100   -0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  1  0
  7  8  2  0
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  9 10  1  6
  9 42  1  0
 42 43  1  6
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 41 15  2  0
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 17 18  1  0
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 11  9  1  0
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 35 66  1  0
 37 67  1  0
 37 68  1  0
 37 69  1  0
 38 70  1  0
 40 71  1  0
 12 50  1  0
M  END


  Mrv1533004231518552D          

 44 49  0  0  0  0            999 V2000
    5.1000    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170    1.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289    1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459    2.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5237    0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077   -1.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6297   -0.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3229   -1.0086    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9102    0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720   -0.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0827    0.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251    1.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379    2.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346    3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473    3.8030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5185    3.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2976    3.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057    2.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615    2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    2.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    3.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9332    4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    3.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090    1.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037    1.2178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    1.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    2.1060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5326    0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -0.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -0.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5581   -0.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709   -1.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    1.5806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295    0.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007    0.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281    1.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    2.0946    0.0000 O   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
 15 41  1  0  0  0  0
  9 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
  5 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CC(=O)C3(Cl)C(C)(C1)C=C(C1=CC(O)C4OC4(CC=C(C)C)C1OC(=O)C1=C(O)C=C(C)C=C1O)C3(O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H33ClO11/c1-14(2)6-7-30-23(43-25(38)22-18(34)8-15(3)9-19(22)35)16(10-20(36)24(30)44-30)17-11-28(4)13-29(27(40)42-5)12-21(37)32(28,33)31(17,41)26(29)39/h6,8-11,20,23-24,34-36,41H,7,12-13H2,1-5H3

> <INCHI_KEY>
OREOZQNTHRYERA-UHFFFAOYSA-N

> <FORMULA>
C32H33ClO11

> <MOLECULAR_WEIGHT>
629.06

> <EXACT_MASS>
628.1711396

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
61.63274172828441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
4.877491007

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.757506627105979

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.639923014416615

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3740664385764294

> <JCHEM_POLAR_SURFACE_AREA>
180.19

> <JCHEM_REFRACTIVITY>
156.4846

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       9.520   0.572   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.178   2.073   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.707   2.528   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.366   4.030   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.578   1.482   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.378   0.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.381  -1.120   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.734  -2.619   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.909  -0.453   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       4.336  -1.883   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       3.566   0.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.121  -1.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.198   0.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.021   0.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.666   1.822   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.100   3.254   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.057   4.460   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.491   5.893   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.448   7.099   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.968   6.118   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.556   6.344   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.011   4.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.421   4.346   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.628   5.303   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.402   6.826   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.609   7.783   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.970   7.392   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.577   3.480   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.380   2.273   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.904   2.499   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.470   3.931   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.861   1.293   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.295  -0.140   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.771  -0.365   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.252  -1.346   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.775  -1.120   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.732  -2.327   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.341   0.312   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.384   1.518   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.950   2.950   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.162   1.209   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.801   0.487   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.279   2.378   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.122   3.910   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   13   43                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   41                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11    5                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   41                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   16   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   39                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   32   40                                                  
CONECT   40   39                                                            
CONECT   41   15    9   42   43                                             
CONECT   42   41                                                            
CONECT   43   41    5   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Value	Source
Methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0,]dec-4-ene-1-carboxylic acid	Generator
Methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₃ClO₁₁

Average Mass

629.0600 Da

Monoisotopic Mass

628.17114 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C12CC(=O)C3(Cl)C(C)(C1)C=C(C1=CC(O)C4OC4(CC=C(C)C)C1OC(=O)C1=C(O)C=C(C)C=C1O)C3(O)C2=O

InChI Identifier

InChI=1S/C32H33ClO11/c1-14(2)6-7-30-23(43-25(38)22-18(34)8-15(3)9-19(22)35)16(10-20(36)24(30)44-30)17-11-28(4)13-29(27(40)42-5)12-21(37)32(28,33)31(17,41)26(29)39/h6,8-11,20,23-24,34-36,41H,7,12-13H2,1-5H3

InChI Key

OREOZQNTHRYERA-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 o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
M-cresol
Resorcinol
Benzoyl
Toluene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Cyclic alcohol
Vinylogous acid
Methyl ester
Tertiary alcohol
Alpha-haloketone
Alpha-chloroketone
Halohydrin
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Ketone
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Oxirane
Ether
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organochloride
Organohalogen compound
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	2.62	ALOGPS
logP	4.88	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	180.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	156.48 m³·mol⁻¹	ChemAxon
Polarizability	61.63 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

75090745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate (NP0327586)

MOL for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

3D MOL for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

3D SDF for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

3D-SDF for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

PDB for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

3D PDB for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

SMILES for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

INCHI for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

Structure for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)

3D Structure for NP0327586 (methyl 7-chloro-4-[2-(2,6-dihydroxy-4-methylbenzoyloxy)-5-hydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-3-hydroxy-6-methyl-2,8-dioxotricyclo[4.3.1.0³,⁷]dec-4-ene-1-carboxylate)