Methyl 3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate

ID: ALA1765412

PubChem CID: 54586132

Max Phase: Preclinical

Molecular Formula: C15H10O6

Molecular Weight: 286.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(O)cc2oc3cccc(O)c3c(=O)c12

Standard InChI:  InChI=1S/C15H10O6/c1-20-15(19)8-5-7(16)6-11-12(8)14(18)13-9(17)3-2-4-10(13)21-11/h2-6,16-17H,1H3

Standard InChI Key:  YBQTVIMCHXORHO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   18.0475   -6.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0475   -4.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3335   -6.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3361   -5.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6271   -4.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9113   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9127   -6.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6261   -6.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7616   -5.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7599   -6.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4732   -6.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1886   -6.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1862   -5.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4723   -4.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6288   -3.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0460   -3.9800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9058   -6.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4710   -3.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1868   -3.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7533   -3.5706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9046   -3.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  3  1  1  0
 10 11  1  0
  4  5  1  0
 11 12  2  0
  1 10  1  0
 12 13  1  0
  5  6  2  0
 13 14  2  0
 14  9  1  0
  9  2  1  0
  5 15  1  0
  6  7  1  0
  2 16  2  0
 12 17  1  0
  7  8  2  0
  8  3  1  0
  4  2  1  0
 18 19  1  0
 18 20  2  0
 14 18  1  0
  3  4  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765412

   Methyl 3,8-dihydroxy-9-oxoxanthene-1-carboxylate

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: 286.24

Molecular Weight (Monoisotopic): 286.0477

AlogP: 2.14

#Rotatable Bonds: 1

Polar Surface Area: 96.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.21

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: 2.58

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: 1.15

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