Microdiplodiasolol

ID: ALA1765411

Cas Number: 1266115-29-0

PubChem CID: 52937072

Max Phase: Preclinical

Molecular Formula: C16H16O7

Molecular Weight: 320.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Microdiplodiasolol | (-)-microdiplodiasolol|CHEBI:68285|Microdiplodiasolol|CHEMBL1765411|DTXSID101118354|Q27136779|1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione|(1S,4aS,9aS)-1,8,9a-trihydroxy-4-methoxy-4a,6-dimethyl-4a,9a-dihydro-1H-xanthene-2,9-dione|1266115-29-0|1H-Xanthene-2,9-dione, 4a,9a-dihydro-1,8,9a-trihydroxy-4-methoxy-4a,6-dimethyl-, (1S,4aS,9aS)-

Canonical SMILES:  COC1=CC(=O)[C@@H](O)[C@@]2(O)C(=O)c3c(O)cc(C)cc3O[C@]12C

Standard InChI:  InChI=1S/C16H16O7/c1-7-4-8(17)12-10(5-7)23-15(2)11(22-3)6-9(18)13(19)16(15,21)14(12)20/h4-6,13,17,19,21H,1-3H3/t13-,15-,16-/m1/s1

Standard InChI Key:  SIUXYUWNLUKHJD-FVQBIDKESA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   16.8690    0.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8678   -0.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5795   -0.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5778    0.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2898    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2930   -0.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0090   -0.8753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0026    0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7232    0.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7228   -0.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4383   -0.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1588   -0.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1592    0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4391    0.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1558   -0.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5755    1.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9982    1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7156    1.1939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4383    1.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4367   -1.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7156   -1.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7243   -2.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8715    0.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
  1  2  2  0
  2 15  1  0
  5  8  1  0
  4 16  1  0
  6  7  1  0
  8 17  2  0
  7 10  1  0
  9 18  1  1
  9  8  1  0
 14 19  1  6
  9 10  1  0
 11 20  1  0
  5  4  2  0
 10 21  1  6
  4  1  1  0
 20 22  1  0
  5  6  1  0
 13 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765411

   MICRODIPLODIASOLOL

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: 320.30

Molecular Weight (Monoisotopic): 320.0896

AlogP: 0.24

#Rotatable Bonds: 1

Polar Surface Area: 113.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: 1.00

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: 2.49

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