polybrominated diphenyl ether derivative

ID: ALA360190

Chembl Id: CHEMBL360190

Max Phase: Preclinical

Molecular Formula: C34H26Br4N4O8

Molecular Weight: 938.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bastadin 7 | Bastadin-7 | Bastadins 7

Canonical SMILES:  O=C1N/C=C/c2ccc(c(Br)c2)Oc2cc(cc(Br)c2O)CCNC(=O)/C(=N/O)Cc2ccc(c(Br)c2)Oc2cc(cc(Br)c2O)C/C1=N\O

Standard InChI:  InChI=1S/C34H26Br4N4O8/c35-21-9-17-1-3-27(21)49-29-15-19(11-23(37)31(29)43)6-8-40-33(45)25(41-47)13-18-2-4-28(22(36)10-18)50-30-16-20(12-24(38)32(30)44)14-26(42-48)34(46)39-7-5-17/h1-5,7,9-12,15-16,43-44,47-48H,6,8,13-14H2,(H,39,46)(H,40,45)/b7-5+,41-25+,42-26+

Standard InChI Key:  ZDBNBLMYAGHTJD-HIHPLZGUSA-N

Alternative Forms

1. Parent:

   

   ALA360190

   BASTADIN 7

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: 938.22

Molecular Weight (Monoisotopic): 933.8484

AlogP: 7.94

#Rotatable Bonds: ┄

Polar Surface Area: 182.30

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 6.71

CX Basic pKa: ┄

CX LogP: 8.30

CX LogD: 7.05

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.08

Np Likeness Score: 1.49

References

1. Segraves EN, Shah RR, Segraves NL, Johnson TA, Whitman S, Sui JK, Kenyon VA, Cichewicz RH, Crews P, Holman TR..  (2004)  Probing the activity differences of simple and complex brominated aryl compounds against 15-soybean, 15-human, and 12-human lipoxygenase.,  47  (16): [PMID:15267244] [10.1021/jm049872s]

2. Greve H, Kehraus S, Krick A, Kelter G, Maier A, Fiebig HH, Wright AD, König GM..  (2008)  Cytotoxic bastadin 24 from the Australian sponge Ianthella quadrangulata.,  71  (3): [PMID:18298075] [10.1021/np070373e]

3. Zieminska E, Lazarewicz JW, Couladouros EA, Moutsos VI, Pitsinos EN..  (2008)  Open-chain half-bastadins mimic the effects of cyclic bastadins on calcium homeostasis in cultured neurons.,  18  (21): [PMID:18851910] [10.1016/j.bmcl.2008.09.080]

4. Calcul L, Inman WD, Morris AA, Tenney K, Ratnam J, McKerrow JH, Valeriote FA, Crews P..  (2010)  Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations.,  73  (3): [PMID:20102170] [10.1021/np9005986]

5. Niemann H, Lin W, Müller WE, Kubbutat M, Lai D, Proksch P..  (2013)  Trimeric hemibastadin congener from the marine sponge Ianthella basta.,  76  (1): [PMID:23249297] [10.1021/np300764u]

6. Bedos-Belval F, Rouch A, Vanucci-Bacque C, Baltas M.  (2012)  Diaryl ether derivatives as anticancer agents a review,  3  (11): [10.1039/C2MD20199B]

7. Eguchi K, Kato H, Fujiwara Y, Losung F, Mangindaan RE, de Voogd NJ, Takeya M, Tsukamoto S..  (2015)  Bastadins, brominated-tyrosine derivatives, suppress accumulation of cholesterol ester in macrophages.,  25  (22): [PMID:26403929] [10.1016/j.bmcl.2015.09.024]

Source

Source(1):

• Scientific Literature