methyl tri-O-methylbrevifolin carboxylate

ID: ALA567497

PubChem CID: 45487725

Max Phase: Preclinical

Molecular Formula: C16H14O8

Molecular Weight: 334.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Methyl Tri-O-Methylbrevifolin Carboxylate | CHEMBL567497|BDBM50415050|methyl tri-O-methylbrevifolin carboxylate

Canonical SMILES:  COC(=O)C1CC(=O)c2oc(=O)c3cc(O)c(OC)c(OC)c3c21

Standard InChI:  InChI=1S/C16H14O8/c1-21-13-9(18)5-7-11(14(13)22-2)10-6(15(19)23-3)4-8(17)12(10)24-16(7)20/h5-6,18H,4H2,1-3H3

Standard InChI Key:  CMUWVXAFOAEMLK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.9757   -5.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9745   -6.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6889   -7.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6871   -5.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4019   -5.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4008   -6.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8326   -5.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1156   -5.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2616   -5.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2602   -7.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1156   -4.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6905   -7.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8321   -6.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1135   -6.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2853   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1103   -7.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4482   -7.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2547   -6.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8884   -8.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0641   -8.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3157   -9.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9187   -9.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774   -8.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5466   -6.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  2  0
  3 12  1  0
 13 14  2  0
  2  3  1  0
  3  6  2  0
  1  2  2  0
  5  8  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 13  7  1  0
 17 18  2  0
  7  8  1  0
 15 19  1  0
  5  4  2  0
 19 20  2  0
  1  9  1  0
 19 21  1  0
  4  1  1  0
 21 22  1  0
  2 10  1  0
 12 23  1  0
  5  6  1  0
 10 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA567497

   methyl tri-O-methylbrevifolin carboxylate

Molecule Features

Natural Product: No

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: 334.28

Molecular Weight (Monoisotopic): 334.0689

AlogP: 1.36

#Rotatable Bonds: 3

Polar Surface Area: 112.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.45

CX Basic pKa: ┄

CX LogP: 0.85

CX LogD: 0.58

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: 1.48

References

1. Gayosso-De-Lucio J, Torres-Valencia M, Rojo-Domínguez A, Nájera-Peña H, Aguirre-López B, Salas-Pacheco J, Avitia-Domínguez C, Téllez-Valencia A..  (2009)  Selective inactivation of triosephosphate isomerase from Trypanosoma cruzi by brevifolin carboxylate derivatives isolated from Geranium bellum Rose.,  19  (20): [PMID:19733070] [10.1016/j.bmcl.2009.08.055]

Source

Source(1):

• Scientific Literature