Mimocaesalpin A; 6-(beta-boivinopyranosyl)apigenin

ID: ALA5291331

Max Phase: Preclinical

Molecular Formula: C21H20O8

Molecular Weight: 400.38

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](c2c(O)cc3oc(-c4ccc(O)cc4)cc(=O)c3c2O)C[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C21H20O8/c1-9-20(26)14(25)8-16(28-9)18-13(24)7-17-19(21(18)27)12(23)6-15(29-17)10-2-4-11(22)5-3-10/h2-7,9,14,16,20,22,24-27H,8H2,1H3/t9-,14+,16-,20+/m1/s1

Standard InChI Key:  NORMTIXLPBZOKX-WPXQMERTSA-N

Molfile:  

 
     RDKit          2D

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   -0.0007    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -0.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1431    1.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562    2.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5711    2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    1.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2857    2.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1418   -1.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2857   -1.6512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -2.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 19 18  2  0
 17 20  1  0
 21  6  1  6
 21 22  1  0
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 21 26  1  0
 26 25  1  0
 25 27  1  1
 24 28  1  6
 23 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5291331

   ---

Molecule Features

Natural Product: Yes

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: 400.38

Molecular Weight (Monoisotopic): 400.1158

AlogP: 2.15

#Rotatable Bonds: 2

Polar Surface Area: 140.59

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.16

CX Basic pKa: ┄

CX LogP: 1.69

CX LogD: 0.31

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: 2.11

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