NP-MRD: Showing NP-Card for Sphaerolone (NP0003382)

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Record Information

Version

1.0

Created at

2020-12-09 00:39:30 UTC

Updated at

2021-07-15 16:46:17 UTC

NP-MRD ID

NP0003382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sphaerolone

Provided By

NPAtlas

Description

7,13,17-Trihydroxy-12-oxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁶,²¹]Henicosa-1,3(8),4,6,10,16(21),17,19-octaene-9,15-dione belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. Sphaerolone is found in Daldinia and Sphaeropsidales sp.strain F-24'707. It was first documented in 2000 (PMID: 10963453). Based on a literature review very few articles have been published on 7,13,17-trihydroxy-12-oxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁶,²¹]Henicosa-1,3(8),4,6,10,16(21),17,19-octaene-9,15-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 38 42  0  0  0  0            999 V2000
   -3.5297   -2.4433   -2.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5793   -1.8215   -1.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -2.0316   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3679   -2.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -1.3374   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -1.0899   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2803   -2.1881   -0.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.8997   -0.8566 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3151   -0.4701    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -1.0763    1.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    0.7500    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    1.6579    1.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739    1.3706    2.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    2.8379    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    3.0589    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    2.1499    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.9587    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886    0.0178   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.4223   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.1957   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.5472    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    0.6019    1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853   -0.0819    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.8475   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805   -1.5577   -0.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.9087   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -2.7245   -3.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -2.9753   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5982   -0.1839   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -1.9047   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8456    2.0036    2.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    3.5486    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    4.0074    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    2.3896    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    1.0158    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.1900    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2904   -0.0696    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0104   -1.5084   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26  2  1  0  0  0  0
 19  4  1  0  0  0  0
 26 20  1  0  0  0  0
 18  6  1  0  0  0  0
 17 11  1  0  0  0  0
  3 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
 25 38  1  0  0  0  0
M  END

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.5297   -2.4433   -2.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5793   -1.8215   -1.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -2.0316   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3679   -2.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -1.3374   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -1.0899   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2803   -2.1881   -0.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.8997   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -0.4701    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -1.0763    1.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    0.7500    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    1.6579    1.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739    1.3706    2.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    2.8379    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    3.0589    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    2.1499    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.9587    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886    0.0178   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.4223   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.1957   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.5472    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    0.6019    1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853   -0.0819    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.8475   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805   -1.5577   -0.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.9087   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -2.7245   -3.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -2.9753   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5982   -0.1839   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -1.9047   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8456    2.0036    2.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    3.5486    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    4.0074    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    2.3896    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    1.0158    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.1900    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2904   -0.0696    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0104   -1.5084   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 19  4  1  0
 26 20  1  0
 18  6  1  0
 17 11  1  0
  3 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
 25 38  1  0
M  END


  Mrv1652306242117473D          

 38 42  0  0  0  0            999 V2000
   -3.5297   -2.4433   -2.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5793   -1.8215   -1.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -2.0316   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3679   -2.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -1.3374   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -1.0899   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2803   -2.1881   -0.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.8997   -0.8566 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3151   -0.4701    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -1.0763    1.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    0.7500    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    1.6579    1.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739    1.3706    2.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    2.8379    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    3.0589    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    2.1499    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.9587    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886    0.0178   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.4223   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.1957   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.5472    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    0.6019    1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853   -0.0819    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.8475   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805   -1.5577   -0.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.9087   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -2.7245   -3.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -2.9753   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5982   -0.1839   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -1.9047   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8456    2.0036    2.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    3.5486    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    4.0074    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    2.3896    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    1.0158    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.1900    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2904   -0.0696    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0104   -1.5084   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26  2  1  0  0  0  0
 19  4  1  0  0  0  0
 26 20  1  0  0  0  0
 18  6  1  0  0  0  0
 17 11  1  0  0  0  0
  3 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 13 31  1  0  0  0  0
 14 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
 25 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C3O[C@]4(O[H])C(=C3C2=C([H])C([H])=C1[H])C1=C([H])C([H])=C([H])C(O[H])=C1C(=O)C4([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O6/c21-11-5-1-3-9-16(11)13(23)7-15-18(9)19-10-4-2-6-12(22)17(10)14(24)8-20(19,25)26-15/h1-7,21-22,25H,8H2/t20-/m0/s1

> <INCHI_KEY>
OEPGXEJLGRYQSA-UHFFFAOYSA-N

> <FORMULA>
C20H12O6

> <MOLECULAR_WEIGHT>
348.31

> <EXACT_MASS>
348.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
34.51605654857341

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13S)-7,13,17-trihydroxy-12-oxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{16,21}]henicosa-1,3,5,7,10,16,18,20-octaene-9,15-dione

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.9983164139999996

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.825797180647028

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.224102917000932

> <JCHEM_PKA_STRONGEST_BASIC>
-4.548184046392035

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
93.59590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13S)-7,13,17-trihydroxy-12-oxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{16,21}]henicosa-1,3,5,7,10,16,18,20-octaene-9,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.5297   -2.4433   -2.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5793   -1.8215   -1.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -2.0316   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3679   -2.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -1.3374   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -1.0899   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2803   -2.1881   -0.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.8997   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -0.4701    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -1.0763    1.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    0.7500    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    1.6579    1.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739    1.3706    2.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    2.8379    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    3.0589    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    2.1499    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.9587    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886    0.0178   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.4223   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.1957   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.5472    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    0.6019    1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853   -0.0819    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.8475   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805   -1.5577   -0.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.9087   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -2.7245   -3.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -2.9753   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5982   -0.1839   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -1.9047   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8456    2.0036    2.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    3.5486    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    4.0074    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    2.3896    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    1.0158    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.1900    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2904   -0.0696    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0104   -1.5084   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 19  4  1  0
 26 20  1  0
 18  6  1  0
 17 11  1  0
  3 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
 25 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  O   UNK     0      -3.530  -2.443  -2.493  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.579  -1.821  -1.984  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.244  -2.032  -2.549  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.266  -1.368  -2.007  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.140  -1.337  -2.311  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.738  -1.090  -1.099  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.280  -2.188  -0.203  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.140  -0.900  -0.857  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.315  -0.470   0.595  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.018  -1.076   1.365  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.545   0.750   0.940  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.136   1.658   1.786  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.374   1.371   2.365  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.457   2.838   2.029  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220   3.059   1.414  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.633   2.150   0.573  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.325   0.959   0.347  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.789   0.018  -0.572  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.415  -0.422  -0.867  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.716  -0.196  -0.273  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.976   0.547   0.849  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.249   0.602   1.373  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.285  -0.082   0.797  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.052  -0.848  -0.330  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.080  -1.558  -0.942  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.769  -0.909  -0.862  0.00  0.00           C+0
HETATM   27  H   UNK     0      -1.109  -2.724  -3.393  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.667  -2.975  -0.670  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.598  -0.184  -1.555  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.655  -1.905  -0.919  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.846   2.004   2.992  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.910   3.549   2.689  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.736   4.007   1.638  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.289   2.390   0.040  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.206   1.016   1.399  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.452   1.190   2.253  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.290  -0.070   1.161  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.010  -1.508  -0.550  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   18                                             
CONECT    7    6   28                                                       
CONECT    8    6    9   29   30                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   31                                                       
CONECT   14   12   15   32                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18   11                                                  
CONECT   18   17   19    6                                                  
CONECT   19   18   20    4                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   23   36                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   38                                                       
CONECT   26   24    2   20                                                  
CONECT   27    3                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
CONECT   38   25                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

RDKit          3D

38 42  0  0  0  0  0  0  0  0999 V2000
   -3.5297   -2.4433   -2.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5793   -1.8215   -1.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -2.0316   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3679   -2.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -1.3374   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -1.0899   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2803   -2.1881   -0.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.8997   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -0.4701    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -1.0763    1.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    0.7500    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    1.6579    1.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739    1.3706    2.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566    2.8379    2.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    3.0589    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    2.1499    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.9587    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886    0.0178   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.4223   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.1957   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.5472    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    0.6019    1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853   -0.0819    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.8475   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805   -1.5577   -0.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.9087   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -2.7245   -3.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -2.9753   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5982   -0.1839   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -1.9047   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8456    2.0036    2.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    3.5486    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    4.0074    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    2.3896    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    1.0158    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.1900    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2904   -0.0696    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0104   -1.5084   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 19  4  1  0
 26 20  1  0
 18  6  1  0
 17 11  1  0
  3 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
 25 38  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₁₂O₆

Average Mass

348.3100 Da

Monoisotopic Mass

348.06339 Da

IUPAC Name

(13S)-7,13,17-trihydroxy-12-oxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{16,21}]henicosa-1,3,5,7,10,16,18,20-octaene-9,15-dione

Traditional Name

(13S)-7,13,17-trihydroxy-12-oxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{16,21}]henicosa-1,3,5,7,10,16,18,20-octaene-9,15-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1C(=O)CC1(O)OC3=CC(=O)C4=C(C=CC=C4O)C3=C21

InChI Identifier

InChI=1S/C20H12O6/c21-11-5-1-3-9-16(11)13(23)7-15-18(9)19-10-4-2-6-12(22)17(10)14(24)8-20(19,25)26-15/h1-7,21-22,25H,8H2

InChI Key

OEPGXEJLGRYQSA-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
Daldinia	NPAtlas	10963453
Sphaeropsidales sp.strain F-24'707	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Naphthalene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dihydrofuran
Vinylogous ester
Vinylogous acid
Hemiacetal
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	3.02	ALOGPS
logP	3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	34.52 Å³	ChemAxon
Number of Rings	5	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

NPA015848

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101724972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bode HB, Zeeck A: Sphaerolone and dihydrosphaerolone, two bisnaphthyl-pigments from the fungus Sphaeropsidales sp. F-24'707. Phytochemistry. 2000 Jul;54(6):597-601. doi: 10.1016/s0031-9422(00)00145-x. [PubMed:10963453 ]

Showing NP-Card for Sphaerolone (NP0003382)

MOL for NP0003382 (Sphaerolone)

3D MOL for NP0003382 (Sphaerolone)

3D SDF for NP0003382 (Sphaerolone)

3D-SDF for NP0003382 (Sphaerolone)

PDB for NP0003382 (Sphaerolone)

3D PDB for NP0003382 (Sphaerolone)

SMILES for NP0003382 (Sphaerolone)

INCHI for NP0003382 (Sphaerolone)

Structure for NP0003382 (Sphaerolone)

3D Structure for NP0003382 (Sphaerolone)