Mimocaesalpin D; (E)-8-(2-carboxyethenyl)apigenin

ID: ALA5288735

Max Phase: Preclinical

Molecular Formula: C18H12O7

Molecular Weight: 340.29

Names and Identifiers

Canonical SMILES:  O=C(O)/C=C/c1c(O)cc(O)c2c(=O)cc(-c3ccc(O)cc3)oc12

Standard InChI:  InChI=1S/C18H12O7/c19-10-3-1-9(2-4-10)15-8-14(22)17-13(21)7-12(20)11(18(17)25-15)5-6-16(23)24/h1-8,19-21H,(H,23,24)/b6-5+

Standard InChI Key:  JJAFIPSOEBHEJK-AATRIKPKSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.4991   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -1.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580    0.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827   -2.4744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    1.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7889   -0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2138    1.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992    2.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138    2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  1 11  1  0
  5 12  1  0
 10 13  2  0
 14  8  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 14 19  1  0
 19 18  2  0
 17 20  1  0
  2 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5288735

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 340.29

Molecular Weight (Monoisotopic): 340.0583

AlogP: 2.67

#Rotatable Bonds: 3

Polar Surface Area: 128.20

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.00

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: -1.56

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: 1.25

References

1. Dias Silva MJ, Simonet AM, Silva NC, Dias ALT, Vilegas W, Macías FA..  (2019)  Bioassay-Guided Isolation of Fungistatic Compounds from Mimosa caesalpiniifolia Leaves.,  82  (6.0): [PMID:31244146] [10.1021/acs.jnatprod.8b01025]

Source

Source(1):

• Scientific Literature