NP-MRD: Showing NP-Card for GEODIN (NP0006403)

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Record Information

Version

2.0

Created at

2020-12-09 03:25:44 UTC

Updated at

2021-07-15 16:54:42 UTC

NP-MRD ID

NP0006403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

GEODIN

Provided By

NPAtlas

Description

GEODIN is found in Aspergillus terreus and Aspergillus terreus IMI16043 . GEODIN was first documented in 1936 (PMID: 16746160). Based on a literature review very few articles have been published on methyl 5,7-dichloro-4-hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-2'-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 38 40  0  0  0  0            999 V2000
   -2.2141    4.4485   -2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.1398   -1.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    2.2889   -1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4374    2.6538   -0.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    0.9340   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    0.5420   -0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -0.7606   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -1.0375   -0.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908   -1.6788    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -1.2863    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092   -2.2508    0.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5970   -3.5135    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.0271   -0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1268   -0.2039   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.3056   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306   -0.8513   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524   -1.5671   -1.9179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -0.8030    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153   -1.3812    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -0.2444    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -0.1919    3.1095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2968    2.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.8779    3.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841    0.2611    1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.7496    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    1.5656    1.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570    4.8813   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    4.4318   -3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    5.1033   -2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    1.2411   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -2.6692    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.9771    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719   -3.3438   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629   -4.0861    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470   -0.9844   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984   -2.4758    0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213   -1.0965    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395    1.2661    3.4780 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  2  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
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 13  5  1  0  0  0  0
 24 15  1  0  0  0  0
 25 13  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  6 30  1  0  0  0  0
  9 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 23 38  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.2141    4.4485   -2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.1398   -1.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    2.2889   -1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4374    2.6538   -0.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    0.9340   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    0.5420   -0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -0.7606   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -1.0375   -0.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908   -1.6788    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -1.2863    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092   -2.2508    0.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5970   -3.5135    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.0271   -0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1268   -0.2039   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.3056   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306   -0.8513   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524   -1.5671   -1.9179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -0.8030    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153   -1.3812    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -0.2444    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -0.1919    3.1095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2968    2.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.8779    3.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841    0.2611    1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.7496    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    1.5656    1.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570    4.8813   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    4.4318   -3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    5.1033   -2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    1.2411   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -2.6692    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.9771    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719   -3.3438   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629   -4.0861    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470   -0.9844   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984   -2.4758    0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213   -1.0965    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395    1.2661    3.4780 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  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 13  5  1  0
 24 15  1  0
 25 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 23 38  1  0
M  END


  Mrv1652306242118273D          

 38 40  0  0  0  0            999 V2000
   -2.2141    4.4485   -2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.1398   -1.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    2.2889   -1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4374    2.6538   -0.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    0.9340   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    0.5420   -0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -0.7606   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -1.0375   -0.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908   -1.6788    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -1.2863    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092   -2.2508    0.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5970   -3.5135    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.0271   -0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1268   -0.2039   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.3056   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306   -0.8513   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524   -1.5671   -1.9179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -0.8030    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153   -1.3812    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -0.2444    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -0.1919    3.1095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2968    2.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.8779    3.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841    0.2611    1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.7496    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    1.5656    1.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570    4.8813   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    4.4318   -3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    5.1033   -2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    1.2411   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -2.6692    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.9771    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719   -3.3438   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629   -4.0861    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470   -0.9844   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984   -2.4758    0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213   -1.0965    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395    1.2661    3.4780 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  2  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
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 13  5  1  0  0  0  0
 24 15  1  0  0  0  0
 25 13  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  6 30  1  0  0  0  0
  9 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 23 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)[C@@]3(OC2=C(Cl)C(=C1Cl)C([H])([H])[H])C(OC([H])([H])[H])=C([H])C(=O)C([H])=C3C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H12Cl2O7/c1-6-11(18)13(21)10-14(12(6)19)26-17(15(10)22)8(16(23)25-3)4-7(20)5-9(17)24-2/h4-5,21H,1-3H3/t17-/m0/s1

> <INCHI_KEY>
LUBKKVGXMXTXOZ-UHFFFAOYSA-N

> <FORMULA>
C17H12Cl2O7

> <MOLECULAR_WEIGHT>
399.18

> <EXACT_MASS>
397.9960081

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
36.55901233130269

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S)-5,7-dichloro-4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.5544201170000003

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.691697211323403

> <JCHEM_PKA_STRONGEST_BASIC>
-4.652852774961251

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
93.98239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-5,7-dichloro-4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxospiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.2141    4.4485   -2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.1398   -1.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    2.2889   -1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4374    2.6538   -0.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    0.9340   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    0.5420   -0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -0.7606   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -1.0375   -0.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908   -1.6788    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -1.2863    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092   -2.2508    0.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5970   -3.5135    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.0271   -0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1268   -0.2039   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.3056   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306   -0.8513   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524   -1.5671   -1.9179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -0.8030    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153   -1.3812    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -0.2444    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -0.1919    3.1095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2968    2.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.8779    3.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841    0.2611    1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.7496    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    1.5656    1.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570    4.8813   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    4.4318   -3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    5.1033   -2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    1.2411   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -2.6692    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.9771    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719   -3.3438   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629   -4.0861    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470   -0.9844   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984   -2.4758    0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213   -1.0965    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395    1.2661    3.4780 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  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
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 11 12  1  0
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 13 14  1  6
 14 15  1  0
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 13  5  1  0
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  1 27  1  0
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  6 30  1  0
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 12 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 23 38  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      -2.214   4.449  -2.164  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.530   3.140  -1.727  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.621   2.289  -1.148  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.437   2.654  -0.981  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.974   0.934  -0.701  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.224   0.542  -0.875  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.736  -0.761  -0.491  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.941  -1.038  -0.699  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.791  -1.679   0.124  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.539  -1.286   0.298  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.709  -2.251   0.901  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.597  -3.514   0.304  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.007   0.027  -0.085  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.127  -0.204  -0.915  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.256  -0.306  -0.127  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.531  -0.851  -0.357  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       2.852  -1.567  -1.918  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       3.457  -0.803   0.632  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.815  -1.381   0.395  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.202  -0.244   1.846  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       4.412  -0.192   3.110  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       1.959   0.297   2.094  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.638   0.878   3.305  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.984   0.261   1.093  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.399   0.750   1.073  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.900   1.566   1.851  0.00  0.00           O+0
HETATM   27  H   UNK     0      -1.557   4.881  -1.356  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.608   4.432  -3.093  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.093   5.103  -2.213  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.927   1.241  -1.339  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.142  -2.669   0.426  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.583  -3.977   0.265  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.172  -3.344  -0.728  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.163  -4.086   0.873  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.247  -0.984  -0.543  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.798  -2.476   0.353  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.521  -1.097   1.208  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.740   1.266   3.478  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   31                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11   32   33   34                                             
CONECT   13   10   14    5   25                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18   35   36   37                                             
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   38                                                       
CONECT   24   22   25   15                                                  
CONECT   25   24   26   13                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    6                                                            
CONECT   31    9                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
CONECT   38   23                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
   -2.2141    4.4485   -2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.1398   -1.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    2.2889   -1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4374    2.6538   -0.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    0.9340   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    0.5420   -0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -0.7606   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408   -1.0375   -0.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908   -1.6788    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -1.2863    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092   -2.2508    0.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5970   -3.5135    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.0271   -0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1268   -0.2039   -0.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.3056   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306   -0.8513   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524   -1.5671   -1.9179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -0.8030    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153   -1.3812    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -0.2444    1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -0.1919    3.1095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2968    2.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.8779    3.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841    0.2611    1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.7496    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    1.5656    1.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570    4.8813   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    4.4318   -3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    5.1033   -2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    1.2411   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -2.6692    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.9771    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719   -3.3438   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629   -4.0861    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470   -0.9844   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984   -2.4758    0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213   -1.0965    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395    1.2661    3.4780 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  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
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 13 14  1  6
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 13  5  1  0
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  6 30  1  0
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 19 35  1  0
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 23 38  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 5,7-dichloro-4-hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-2'-carboxylic acid	Generator
Estin	MeSH

Chemical Formula

C₁₇H₁₂Cl₂O₇

Average Mass

399.1800 Da

Monoisotopic Mass

397.99601 Da

IUPAC Name

methyl (2S)-5,7-dichloro-4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

Traditional Name

methyl (2S)-5,7-dichloro-4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxospiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(=O)C=C(OC)C11OC2=C(C1=O)C(O)=C(Cl)C(C)=C2Cl

InChI Identifier

InChI=1S/C17H12Cl2O7/c1-6-11(18)13(21)10-14(12(6)19)26-17(15(10)22)8(16(23)25-3)4-7(20)5-9(17)24-2/h4-5,21H,1-3H3

InChI Key

LUBKKVGXMXTXOZ-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
Aspergillus terreus	NPAtlas	16746160
Aspergillus terreus IMI16043	Fungi	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
Aryl alkyl ketone
Aryl ketone
4-halophenol
2-halophenol
Alkyl aryl ether
Phenol
Aryl chloride
Aryl halide
Benzenoid
Vinylogous ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Cyclic ketone
Ketone
Ether
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organohalogen compound
Organochloride
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	3.41	ALOGPS
logP	3.55	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.69	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.98 m³·mol⁻¹	ChemAxon
Polarizability	36.56 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

NPA017530

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

187606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

216465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raistrick H, Smith G: Studies in the biochemistry of micro-organisms: The metabolic products of Aspergillus terreus Thom. Part II. Two new chlorine-containing mould metabolic products, geodin and erdin. Biochem J. 1936 Aug;30(8):1315-22. doi: 10.1042/bj0301315. [PubMed:16746160 ]

Showing NP-Card for GEODIN (NP0006403)

MOL for NP0006403 (GEODIN)

3D MOL for NP0006403 (GEODIN)

3D SDF for NP0006403 (GEODIN)

3D-SDF for NP0006403 (GEODIN)

PDB for NP0006403 (GEODIN)

3D PDB for NP0006403 (GEODIN)

SMILES for NP0006403 (GEODIN)

INCHI for NP0006403 (GEODIN)

Structure for NP0006403 (GEODIN)

3D Structure for NP0006403 (GEODIN)