NP-MRD: Showing NP-Card for Pseudodeflectusin (NP0005371)

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Record Information

Version

2.0

Created at

2020-12-09 02:38:03 UTC

Updated at

2021-07-15 16:51:48 UTC

NP-MRD ID

NP0005371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pseudodeflectusin

Provided By

NPAtlas

Description

Pseudodeflectusin belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. Pseudodeflectusin is found in Aspergillus pseudodeflectus and Aspergillus versicolor. Pseudodeflectusin was first documented in 2004 (PMID: 15177469). Based on a literature review very few articles have been published on Pseudodeflectusin (PMID: 24033077) (PMID: 23470748) (PMID: 22931431) (PMID: 20699584).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118183D          

 35 37  0  0  0  0            999 V2000
    5.0649   -0.4114   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118   -0.8248    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.7670    1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -0.3467    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -0.6048    0.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.0917   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    0.8447   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.6059   -2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    1.6357   -1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    0.8735   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.0952   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -0.7124    1.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0900    2.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.9313    0.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    0.2727    0.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0959   -0.0883    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9301   -0.8250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4779    0.5765   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    1.0733   -1.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -0.6949    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.7063   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.9334   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -1.8546    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -2.7739    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.2978    2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022    2.1793   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    2.2364   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.7213    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -0.7212    3.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4766    0.9554    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3239   -0.7168   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.7808    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.7176    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    1.9628   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.3878   -1.7081 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
  2  4  2  3  0  0  0
  4  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18  4  1  0  0  0  0
 11  6  1  0  0  0  0
 17 10  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
 12 28  1  1  0  0  0
 13 29  1  0  0  0  0
 15 30  1  1  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.0649   -0.4114   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118   -0.8248    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.7670    1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -0.3467    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -0.6048    0.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.0917   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    0.8447   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.6059   -2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    1.6357   -1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    0.8735   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.0952   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -0.7124    1.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0900    2.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.9313    0.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    0.2727    0.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0959   -0.0883    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9301   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779    0.5765   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    1.0733   -1.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -0.6949    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.7063   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.9334   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -1.8546    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -2.7739    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.2978    2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022    2.1793   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    2.2364   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.7213    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -0.7212    3.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4766    0.9554    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3239   -0.7168   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.7808    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.7176    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    1.9628   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.3878   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7 18  1  0
 18 19  2  0
 18  4  1  0
 11  6  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  1
 13 29  1  0
 15 30  1  1
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END


  Mrv1652306242118183D          

 35 37  0  0  0  0            999 V2000
    5.0649   -0.4114   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118   -0.8248    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.7670    1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -0.3467    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -0.6048    0.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.0917   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    0.8447   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.6059   -2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    1.6357   -1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    0.8735   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.0952   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -0.7124    1.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0900    2.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.9313    0.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    0.2727    0.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0959   -0.0883    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9301   -0.8250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4779    0.5765   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    1.0733   -1.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -0.6949    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.7063   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.9334   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -1.8546    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -2.7739    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.2978    2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022    2.1793   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    2.2364   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.7213    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -0.7212    3.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4766    0.9554    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3239   -0.7168   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.7808    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.7176    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    1.9628   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.3878   -1.7081 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
  2  4  2  3  0  0  0
  4  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18  4  1  0  0  0  0
 11  6  1  0  0  0  0
 17 10  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
 12 28  1  1  0  0  0
 13 29  1  0  0  0  0
 15 30  1  1  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])O[C@]([H])(C([H])([H])[H])C([H])([H])C2=C1C1=C(C([H])=C2[H])C(=O)C(O1)=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-7(2)13-12(16)10-5-4-9-6-8(3)18-15(17)11(9)14(10)19-13/h4-5,8,15,17H,6H2,1-3H3/t8-,15+/m1/s1

> <INCHI_KEY>
LSQCSEQTJDZMSO-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.289

> <EXACT_MASS>
260.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.287989704512803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R,13S)-13-hydroxy-11-methyl-4-(propan-2-ylidene)-3,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),2(6),7-trien-5-one

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
2.1971479410000003

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.230271807208357

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3350507521124975

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
71.5587

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R,13S)-13-hydroxy-11-methyl-4-(propan-2-ylidene)-3,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),2(6),7-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.0649   -0.4114   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118   -0.8248    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.7670    1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -0.3467    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -0.6048    0.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.0917   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    0.8447   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.6059   -2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    1.6357   -1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    0.8735   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.0952   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -0.7124    1.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0900    2.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.9313    0.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    0.2727    0.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0959   -0.0883    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9301   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779    0.5765   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    1.0733   -1.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -0.6949    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.7063   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.9334   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -1.8546    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -2.7739    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.2978    2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022    2.1793   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    2.2364   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.7213    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -0.7212    3.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4766    0.9554    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3239   -0.7168   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.7808    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.7176    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    1.9628   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.3878   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7 18  1  0
 18 19  2  0
 18  4  1  0
 11  6  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  1
 13 29  1  0
 15 30  1  1
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 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       5.065  -0.411  -0.040  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.812  -0.825   0.596  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.858  -1.767   1.744  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.654  -0.347   0.132  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.363  -0.605   0.582  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.429   0.092  -0.173  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   0.845  -1.161  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.286   1.606  -2.012  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.091   1.636  -1.905  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.685   0.874  -0.910  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.958   0.095  -0.034  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.604  -0.712   1.022  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.630  -0.090   2.255  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.924  -0.931   0.630  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.617   0.273   0.468  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.096  -0.088   0.410  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.172   0.930  -0.825  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.478   0.577  -0.980  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.390   1.073  -1.683  0.00  0.00           O+0
HETATM   20  H   UNK     0       5.941  -0.695   0.593  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.136   0.706  -0.173  0.00  0.00           H+0
HETATM   22  H   UNK     0       5.240  -0.933  -1.018  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.854  -1.855   2.217  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.221  -2.774   1.453  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.519  -1.298   2.518  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.802   2.179  -2.767  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.683   2.236  -2.579  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.142  -1.721   1.123  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.542  -0.721   3.012  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.477   0.955   1.314  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.324  -0.717  -0.469  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.750   0.781   0.394  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.287  -0.718   1.306  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.562   1.963  -0.889  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.566   0.388  -1.708  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   23   24   25                                             
CONECT    4    2    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13   14   28                                             
CONECT   13   12   29                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17   30                                             
CONECT   16   15   31   32   33                                             
CONECT   17   15   10   34   35                                             
CONECT   18    7   19    4                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
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
    5.0649   -0.4114   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118   -0.8248    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.7670    1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -0.3467    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -0.6048    0.5818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.0917   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    0.8447   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.6059   -2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    1.6357   -1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    0.8735   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.0952   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -0.7124    1.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6301   -0.0900    2.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.9313    0.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    0.2727    0.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0959   -0.0883    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9301   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779    0.5765   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    1.0733   -1.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -0.6949    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.7063   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.9334   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -1.8546    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -2.7739    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.2978    2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022    2.1793   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    2.2364   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.7213    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -0.7212    3.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4766    0.9554    1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3239   -0.7168   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7501    0.7808    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2871   -0.7176    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    1.9628   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.3878   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7 18  1  0
 18 19  2  0
 18  4  1  0
 11  6  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  1
 13 29  1  0
 15 30  1  1
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Mass

260.2890 Da

Monoisotopic Mass

260.10486 Da

IUPAC Name

(11R,13S)-13-hydroxy-11-methyl-4-(propan-2-ylidene)-3,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),2(6),7-trien-5-one

Traditional Name

(11R,13S)-13-hydroxy-11-methyl-4-(propan-2-ylidene)-3,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),2(6),7-trien-5-one

CAS Registry Number

Not Available

SMILES

CC1CC2=C(C(O)O1)C1=C(C=C2)C(=O)C(O1)=C(C)C

InChI Identifier

InChI=1S/C15H16O4/c1-7(2)13-12(16)10-5-4-9-6-8(3)18-15(17)11(9)14(10)19-13/h4-5,8,15,17H,6H2,1-3H3

InChI Key

LSQCSEQTJDZMSO-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 pseudodeflectus	NPAtlas	15177469
Aspergillus versicolor	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Coumaran
Benzofuran
Aryl ketone
Benzenoid
Ketone
Hemiacetal
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	1.81	ALOGPS
logP	2.2	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.23	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.56 m³·mol⁻¹	ChemAxon
Polarizability	28.29 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

NPA011259

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8620728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10445309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ogawa A, Murakami C, Kamisuki S, Kuriyama I, Yoshida H, Sugawara F, Mizushina Y: Pseudodeflectusin, a novel isochroman derivative from Aspergillus pseudodeflectus a parasite of the sea weed, Sargassum fusiform, as a selective human cancer cytotoxin. Bioorg Med Chem Lett. 2004 Jul 5;14(13):3539-43. doi: 10.1016/j.bmcl.2004.04.050. [PubMed:15177469 ]
Kuramochi K, Tsubaki K, Kuriyama I, Mizushina Y, Yoshida H, Takeuchi T, Kamisuki S, Sugawara F, Kobayashi S: Synthesis, structure, and cytotoxicity studies of some fungal isochromanes. J Nat Prod. 2013 Sep 27;76(9):1737-45. doi: 10.1021/np400460m. Epub 2013 Sep 13. [PubMed:24033077 ]
Kuramochi K: Synthetic and structure-activity relationship studies on bioactive natural products. Biosci Biotechnol Biochem. 2013;77(3):446-54. doi: 10.1271/bbb.120884. Epub 2013 Mar 7. [PubMed:23470748 ]
Maegawa T, Otake K, Hirosawa K, Goto A, Fujioka H: Method for the efficient synthesis of highly-substituted oxetan- and azetidin-, dihydrofuran- and pyrrolidin-3-ones and its application to the synthesis of (+/-)-pseudodeflectusin. Org Lett. 2012 Sep 21;14(18):4798-801. doi: 10.1021/ol302096j. Epub 2012 Aug 29. [PubMed:22931431 ]
Kuramochi K, Saito F, Nakazaki A, Takeuchi T, Tsubaki K, Sugawara F, Kobayashi S: Synthesis of pseudodeflectusin and ustusorane C: structural revision of aspergione a and B. Biosci Biotechnol Biochem. 2010;74(8):1635-40. doi: 10.1271/bbb.100241. Epub 2010 Aug 7. [PubMed:20699584 ]

Showing NP-Card for Pseudodeflectusin (NP0005371)

MOL for NP0005371 (Pseudodeflectusin)

3D MOL for NP0005371 (Pseudodeflectusin)

3D SDF for NP0005371 (Pseudodeflectusin)

3D-SDF for NP0005371 (Pseudodeflectusin)

PDB for NP0005371 (Pseudodeflectusin)

3D PDB for NP0005371 (Pseudodeflectusin)

SMILES for NP0005371 (Pseudodeflectusin)

INCHI for NP0005371 (Pseudodeflectusin)

Structure for NP0005371 (Pseudodeflectusin)

3D Structure for NP0005371 (Pseudodeflectusin)