chrysophaentin A

ID: ALA2418095

PubChem CID: 46872004

Max Phase: Preclinical

Molecular Formula: C32H24Cl4O8

Molecular Weight: 678.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cc(O)c2c(c1)C/C(Cl)=C\Cc1cc(c(Cl)cc1O)Oc1c(O)cc(cc1O)C/C(Cl)=C\Cc1cc(c(Cl)cc1O)O2

Standard InChI:  InChI=1S/C32H24Cl4O8/c33-19-3-1-16-10-29(22(35)13-24(16)38)43-31-18(9-21(37)12-28(31)42)8-20(34)4-2-17-11-30(23(36)14-25(17)39)44-32-26(40)6-15(5-19)7-27(32)41/h3-4,6-7,9-14,37-42H,1-2,5,8H2/b19-3+,20-4+

Standard InChI Key:  QGYSNOUOCKPDTD-KNPOPJAVSA-N

Molfile:  

     RDKit          2D

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  1  2  2  0
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 27 32  1  0
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 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
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 40 44  1  0
 41  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2418095

   Chrysophaentin A

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: 678.35

Molecular Weight (Monoisotopic): 676.0225

AlogP: 8.94

#Rotatable Bonds: ┄

Polar Surface Area: 139.84

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -4.07

CX Basic pKa: 9.21

CX LogP: 8.68

CX LogD: 7.73

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.11

Np Likeness Score: 0.86

References

1. Keffer JL, Huecas S, Hammill JT, Wipf P, Andreu JM, Bewley CA..  (2013)  Chrysophaentins are competitive inhibitors of FtsZ and inhibit Z-ring formation in live bacteria.,  21  (18): [PMID:23932448] [10.1016/j.bmc.2013.07.033]

2. Li X, Ma S..  (2015)  Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.,  95  [PMID:25791674] [10.1016/j.ejmech.2015.03.026]

3. Haranahalli K, Tong S, Ojima I..  (2016)  Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.,  24  (24): [PMID:27189886] [10.1016/j.bmc.2016.05.003]

4. Hurley KA, Santos TM, Nepomuceno GM, Huynh V, Shaw JT, Weibel DB..  (2016)  Targeting the Bacterial Division Protein FtsZ.,  59  (15): [PMID:26756351] [10.1021/acs.jmedchem.5b01098]

Source

Source(1):

• Scientific Literature