Microdiplodiasone

ID: ALA1765410

PubChem CID: 52937071

Max Phase: Preclinical

Molecular Formula: C14H14O6

Molecular Weight: 278.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Microdiplodiasone | (+)-microdiplodiasone|CHEBI:68284|Microdiplodiasone|CHEMBL1765410|(2R,9R)-(+)-microdiplodiasone|Q27136778|(2R)-5,7-dihydroxy-2-methyl-2-[(2R)-5-oxotetrahydrofuran-2-yl]-2,3-dihydro-4H-chromen-4-one

Canonical SMILES:  C[C@]1([C@H]2CCC(=O)O2)CC(=O)c2c(O)cc(O)cc2O1

Standard InChI:  InChI=1S/C14H14O6/c1-14(11-2-3-12(18)19-11)6-9(17)13-8(16)4-7(15)5-10(13)20-14/h4-5,11,15-16H,2-3,6H2,1H3/t11-,14-/m1/s1

Standard InChI Key:  KYUNATJAFQPBJE-BXUZGUMPSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    9.2139    0.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2128   -0.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9272   -0.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9255    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6403    0.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6389   -0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3554   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0779   -0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0792    0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3582    0.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9231    1.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4980   -0.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3584    1.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7911   -0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8711   -1.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6775   -1.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0923   -1.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5420   -0.6410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0717   -1.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7838   -0.1518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9130   -1.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  5  6  1  0
  4 11  1  0
  2 12  1  0
  2  3  1  0
 10 13  2  0
  3  6  2  0
  8 14  1  0
 14 15  1  0
  1  2  2  0
  5  4  2  0
  4  1  1  0
  5 10  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  6  7  1  0
  8 19  1  1
  7  8  1  0
 14 20  1  1
  8  9  1  0
 17 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765410

   MICRODIPLODIASONE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 278.26

Molecular Weight (Monoisotopic): 278.0790

AlogP: 1.53

#Rotatable Bonds: 1

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.87

CX Basic pKa: ┄

CX LogP: 1.73

CX LogD: 1.60

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.76

Np Likeness Score: 2.81

References

1. Siddiqui IN, Zahoor A, Hussain H, Ahmed I, Ahmad VU, Padula D, Draeger S, Schulz B, Meier K, Steinert M, Kurtán T, Flörke U, Pescitelli G, Krohn K..  (2011)  Diversonol and blennolide derivatives from the endophytic fungus Microdiplodia sp.: absolute configuration of diversonol.,  74  (3): [PMID:21244021] [10.1021/np100730b]

Source

Source(1):

• Scientific Literature