NP-MRD: Showing NP-Card for Chloromonilicin (NP0021269)

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Record Information

Version

2.0

Created at

2021-01-06 06:32:13 UTC

Updated at

2021-07-15 17:35:54 UTC

NP-MRD ID

NP0021269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chloromonilicin

Provided By

NPAtlas

Description

Chloromonilicin is found in Monilinia fructicola. Chloromonilicin was first documented in 1985 (PMID: 3839228). Based on a literature review very few articles have been published on Chloromonilicin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120413D          

 35 37  0  0  0  0            999 V2000
   -4.0754    2.5054    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3167    1.5135    0.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    0.2411    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628    0.0287    1.8636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.8130    0.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6708   -2.0565    0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.3567    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534   -4.2838    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -3.6994   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037   -2.9583   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -3.6382   -2.4704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.6511   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.4750   -0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.3830   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061   -0.2307   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.8792   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    0.9689   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836    1.8826    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.7803    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566    2.8240    1.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332    0.6337    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.4577    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175    1.3440    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.6762   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1453    2.2649    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    3.5065    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405    2.3611    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -1.0014   -0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -4.6400   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357   -1.0431   -1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.3578   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5722    2.0065   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    0.5833    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    2.7847    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436    2.9826    1.4237 H   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  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24  5  1  0  0  0  0
 24 12  2  0  0  0  0
 21 14  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  5 28  1  6  0  0  0
  9 29  1  0  0  0  0
 15 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  0  0  0  0
 20 35  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.0754    2.5054    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3167    1.5135    0.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    0.2411    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628    0.0287    1.8636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.8130    0.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6708   -2.0565    0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.3567    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534   -4.2838    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -3.6994   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037   -2.9583   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -3.6382   -2.4704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.6511   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.4750   -0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.3830   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061   -0.2307   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.8792   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    0.9689   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836    1.8826    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.7803    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566    2.8240    1.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332    0.6337    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.4577    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175    1.3440    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.6762   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1453    2.2649    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    3.5065    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405    2.3611    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -1.0014   -0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -4.6400   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357   -1.0431   -1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.3578   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5722    2.0065   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    0.5833    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    2.7847    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436    2.9826    1.4237 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
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 12 13  1  0
 13 14  1  0
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 16 17  1  0
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 24  5  1  0
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 21 14  1  0
  1 25  1  0
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  1 27  1  0
  5 28  1  6
  9 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END


  Mrv1652306242120413D          

 35 37  0  0  0  0            999 V2000
   -4.0754    2.5054    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3167    1.5135    0.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    0.2411    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628    0.0287    1.8636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.8130    0.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6708   -2.0565    0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.3567    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534   -4.2838    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -3.6994   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037   -2.9583   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -3.6382   -2.4704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.6511   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.4750   -0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.3830   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061   -0.2307   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.8792   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    0.9689   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836    1.8826    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.7803    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566    2.8240    1.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332    0.6337    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.4577    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175    1.3440    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.6762   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1453    2.2649    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    3.5065    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405    2.3611    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -1.0014   -0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -4.6400   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357   -1.0431   -1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.3578   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5722    2.0065   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    0.5833    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    2.7847    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436    2.9826    1.4237 H   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  2  0  0  0  0
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 12 13  1  0  0  0  0
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 22 24  1  0  0  0  0
 24  5  1  0  0  0  0
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 21 14  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  5 28  1  6  0  0  0
  9 29  1  0  0  0  0
 15 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  0  0  0  0
 20 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(OC3=C(C2=O)[C@@]([H])(OC(=O)C([H])=C3Cl)C(=O)OC([H])([H])[H])=C([H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H11ClO7/c1-6-3-8(18)11-9(4-6)23-14-7(17)5-10(19)24-15(16(21)22-2)12(14)13(11)20/h3-5,15,18H,1-2H3/t15-/m1/s1

> <INCHI_KEY>
XEADRORPHLTLNQ-UHFFFAOYSA-N

> <FORMULA>
C16H11ClO7

> <MOLECULAR_WEIGHT>
350.71

> <EXACT_MASS>
350.0193304

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
32.76105157697697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R)-5-chloro-10-hydroxy-8-methyl-3,11-dioxo-1H,3H,11H-oxepino[4,3-b]chromene-1-carboxylate

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.617170123333333

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.395994685849331

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.480033840836178

> <JCHEM_PKA_STRONGEST_BASIC>
-5.408938344079974

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
83.81379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R)-5-chloro-10-hydroxy-8-methyl-3,11-dioxo-1H-oxepino[4,3-b]chromene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.0754    2.5054    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3167    1.5135    0.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    0.2411    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628    0.0287    1.8636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.8130    0.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6708   -2.0565    0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.3567    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534   -4.2838    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -3.6994   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037   -2.9583   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -3.6382   -2.4704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.6511   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.4750   -0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.3830   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061   -0.2307   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.8792   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    0.9689   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836    1.8826    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.7803    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566    2.8240    1.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332    0.6337    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.4577    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175    1.3440    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.6762   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1453    2.2649    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    3.5065    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405    2.3611    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -1.0014   -0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -4.6400   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357   -1.0431   -1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.3578   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5722    2.0065   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    0.5833    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    2.7847    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436    2.9826    1.4237 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  5  1  0
 24 12  2  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  6
  9 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.075   2.505   0.928  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.317   1.514   0.219  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.125   0.241   0.738  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.663   0.029   1.864  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.380  -0.813   0.079  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.671  -2.057   0.784  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.474  -3.357   0.279  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.153  -4.284   0.760  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.528  -3.699  -0.770  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.504  -2.958  -1.192  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       0.457  -3.638  -2.470  0.00  0.00          Cl+0
HETATM   12  C   UNK     0      -0.128  -1.651  -0.665  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.158  -1.475  -0.808  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.748  -0.383  -0.407  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.106  -0.231  -0.574  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.790   0.879  -0.182  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.271   0.969  -0.399  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.084   1.883   0.404  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.687   1.780   0.601  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.057   2.824   1.192  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.033   0.634   0.186  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.336   0.458   0.343  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.018   1.344   0.875  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.934  -0.676  -0.078  0.00  0.00           C+0
HETATM   25  H   UNK     0      -5.145   2.265   0.706  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.839   3.506   0.565  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.941   2.361   2.017  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.793  -1.001  -0.976  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.678  -4.640  -1.237  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.636  -1.043  -1.041  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.549   0.358  -1.265  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.572   2.006  -0.616  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.827   0.583   0.502  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.584   2.785   0.733  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.144   2.983   1.424  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   29                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   31   32   33                                             
CONECT   18   16   19   34                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   35                                                       
CONECT   21   19   22   14                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   12                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    5                                                            
CONECT   29    9                                                            
CONECT   30   15                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   20                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -4.0754    2.5054    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3167    1.5135    0.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    0.2411    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628    0.0287    1.8636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.8130    0.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6708   -2.0565    0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.3567    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534   -4.2838    0.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -3.6994   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037   -2.9583   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4574   -3.6382   -2.4704 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.6511   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -1.4750   -0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -0.3830   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061   -0.2307   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.8792   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    0.9689   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836    1.8826    0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.7803    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566    2.8240    1.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332    0.6337    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.4577    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175    1.3440    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.6762   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1453    2.2649    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    3.5065    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405    2.3611    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -1.0014   -0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -4.6400   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357   -1.0431   -1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.3578   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5722    2.0065   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    0.5833    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    2.7847    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436    2.9826    1.4237 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  5  1  0
 24 12  2  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  6
  9 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Chloromonilicin	MeSH
Methyl 5-chloro-10-hydroxy-8-methyl-3,11-dioxo-1H,3H,11H-oxepino[4,3-b]chromene-1-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₁ClO₇

Average Mass

350.7100 Da

Monoisotopic Mass

350.01933 Da

IUPAC Name

methyl (1R)-5-chloro-10-hydroxy-8-methyl-3,11-dioxo-1H,3H,11H-oxepino[4,3-b]chromene-1-carboxylate

Traditional Name

methyl (1R)-5-chloro-10-hydroxy-8-methyl-3,11-dioxo-1H-oxepino[4,3-b]chromene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(=O)C=C(Cl)C2=C1C(=O)C1=C(O2)C=C(C)C=C1O

InChI Identifier

InChI=1S/C16H11ClO7/c1-6-3-8(18)11-9(4-6)23-14-7(17)5-10(19)24-15(16(21)22-2)12(14)13(11)20/h3-5,15,18H,1-2H3

InChI Key

XEADRORPHLTLNQ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Monilinia fructicola	NPAtlas	3839228

Chemical Taxonomy

Classification

Not classified

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	2.54	ALOGPS
logP	2.62	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.81 m³·mol⁻¹	ChemAxon
Polarizability	32.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001827

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018634

Chemspider ID

4589157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5486973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sassa T, Kachi H, Nukina M, Suzuki Y: Chloromonilicin, a new antifungal metabolite produced by Monilinia fructicola. J Antibiot (Tokyo). 1985 Mar;38(3):439-41. doi: 10.7164/antibiotics.38.439. [PubMed:3839228 ]

Showing NP-Card for Chloromonilicin (NP0021269)

MOL for NP0021269 (Chloromonilicin)

3D MOL for NP0021269 (Chloromonilicin)

3D SDF for NP0021269 (Chloromonilicin)

3D-SDF for NP0021269 (Chloromonilicin)

PDB for NP0021269 (Chloromonilicin)

3D PDB for NP0021269 (Chloromonilicin)

SMILES for NP0021269 (Chloromonilicin)

INCHI for NP0021269 (Chloromonilicin)

Structure for NP0021269 (Chloromonilicin)

3D Structure for NP0021269 (Chloromonilicin)