Showing metabocard for Leptosphaerone C (MMDBc0010876)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 02:55:21 UTC
Update Date2025-10-07 16:05:48 UTC
Metabolite IDMMDBc0010876
Metabolite Identification
Common NameLeptosphaerone C
DescriptionLeptosphaerone C is a polyketide metabolite described in biomedical literature. It was isolated from the fungus Penicillium sp., alongside other compounds such as penicillenone, arugosin I, and 9-demethyl FR-901235, as well as five known compounds including bacillosporin A, bacillosporin C, sequoiamonascin D, sequoiatone A, and sequoiatone B (PMID:18067932 ). Polyketides like Leptosphaerone C are known for their diverse biological activities, which can include antimicrobial, antifungal, and anticancer properties. The structural complexity of polyketides arises from their biosynthetic pathways, which involve the assembly of acetate and other building blocks through the action of polyketide synthases. Understanding the chemistry and biological functions of Leptosphaerone C and its related compounds is essential for exploring their potential applications in pharmaceuticals and biotechnology.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x0000564f9faec5c8>


  Mrv1652305152104552D          

 12 12  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  6  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  7 10  1  6  0  0  0
  8 11  1  1  0  0  0
  7 12  1  1  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000564f9faec5c8>

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3D SDF for #<Metabolite:0x0000564f9faec5c8>

  Mrv1652305152104552D          

 12 12  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  6  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  7 10  1  6  0  0  0
  8 11  1  1  0  0  0
  7 12  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0010876

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(O)CC(C)=CC(=O)[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O3/c1-5-3-6(9)8(2,11)7(10)4-5/h3,7,10-11H,4H2,1-2H3/t7-,8-/m1/s1

> <INCHI_KEY>
JPANATRWCFTRDD-HTQZYQBOSA-N

> <FORMULA>
C8H12O3

> <MOLECULAR_WEIGHT>
156.181

> <EXACT_MASS>
156.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.939950344337328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6S)-5,6-dihydroxy-3,6-dimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
-0.58

> <JCHEM_LOGP>
0.21617538433333378

> <ALOGPS_LOGS>
0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.542730878610158

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.310925756114894

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3426570869993544

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.189699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6S)-5,6-dihydroxy-3,6-dimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x0000564f9faec5c8>
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PDB for #<Metabolite:0x0000564f9faec5c8>
HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.517   1.273   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    5    6                                                       
CONECT    4    5    7                                                       
CONECT    5    1    3    4                                                  
CONECT    6    3    8    9                                                  
CONECT    7    4    8   10   12                                             
CONECT    8    2    6    7   11                                             
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for #<Metabolite:0x0000564f9faec5c8>
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SMILES for #<Metabolite:0x0000564f9faec5c8>
[H][C@@]1(O)CC(C)=CC(=O)[C@@]1(C)O
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INCHI for #<Metabolite:0x0000564f9faec5c8>
InChI=1S/C8H12O3/c1-5-3-6(9)8(2,11)7(10)4-5/h3,7,10-11H,4H2,1-2H3/t7-,8-/m1/s1
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Synonyms
ValueSource
(2S,3R)-2,3-Dihydroxy-2,5-dimethylcyclohex-5-enoneMeSH
Molecular FormulaC8H12O3
Average Mass156.181
Monoisotopic Mass156.078644246
IUPAC Name(5R,6S)-5,6-dihydroxy-3,6-dimethylcyclohex-2-en-1-one
Traditional Name(5R,6S)-5,6-dihydroxy-3,6-dimethylcyclohex-2-en-1-one
CAS Registry NumberNot Available
SMILES
[H][C@@]1(O)CC(C)=CC(=O)[C@@]1(C)O
InChI Identifier
InChI=1S/C8H12O3/c1-5-3-6(9)8(2,11)7(10)4-5/h3,7,10-11H,4H2,1-2H3/t7-,8-/m1/s1
InChI KeyJPANATRWCFTRDD-HTQZYQBOSA-N