methylbrevifolin carboxylate

ID: ALA567076

Cas Number: 154702-76-8

PubChem CID: 5319518

Max Phase: Preclinical

Molecular Formula: C14H10O8

Molecular Weight: 306.23

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Methylbrevifolin Carboxylate | Methyl brevifolincarboxylate|154702-76-8|CHEMBL567076|CHEBI:66711|methyl 7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylate|methyl 7,8,9-trihydroxy-3,5-dioxo-1,2,3,5-tetrahydrocyclopenta[c]isochromene-1-carboxylate|methylbrevifolin carboxylate|DTXSID20935047|HY-N7647|BDBM50415047|AKOS040755436|CS-0134956|Q27135333|Methyl 7,8,9-trihydroxy-3,5-dioxo-1,2,3,5-tetrahydrobenzo[d]cyclopenta[b]pyran-1-carboxylate

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

Standard InChI:  InChI=1S/C14H10O8/c1-21-13(19)5-3-7(16)12-9(5)8-4(14(20)22-12)2-6(15)10(17)11(8)18/h2,5,15,17-18H,3H2,1H3

Standard InChI Key:  JNWDNAASYHRXMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -3.6390    1.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6402    1.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261    0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    2.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2134    1.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2145    1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    1.8829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    2.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    3.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9245   -0.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838    1.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5021    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5057   -0.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6382    0.6742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7272   -0.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.9060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -1.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -2.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  5  6  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA567076

   METHYLBREVIFOLIN 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: 306.23

Molecular Weight (Monoisotopic): 306.0376

AlogP: 0.75

#Rotatable Bonds: 1

Polar Surface Area: 134.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.65

CX Basic pKa: ┄

CX LogP: 0.56

CX LogD: -0.33

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.52

Np Likeness Score: 1.64

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]

2. Zheng HC, Lu Y, Chen DF..  (2018)  Anticomplement compounds from Polygonum chinense.,  28  (9): [PMID:29631958] [10.1016/j.bmcl.2018.03.079]

Source

Source(1):

• Scientific Literature