ID: ALA439151

Max Phase: Preclinical

Molecular Formula: C34H27Br5N4O8

Molecular Weight: 1019.13

Molecule Type: Small molecule

Representations

Synonyms (2): Bastadin 5 | Bastadin-5
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C1NCCc2cc(Br)c(O)c(c2)Oc2ccc(cc2Br)CCNC(=O)/C(=N\O)Cc2cc(Br)c(O)c(c2)Oc2c(Br)cc(cc2Br)C/C1=N/O

Standard InChI:  InChI=1S/C34H27Br5N4O8/c35-20-7-16-1-2-27(20)50-28-14-17(8-21(36)30(28)44)4-6-41-33(46)25(42-48)12-18-10-23(38)32(24(39)11-18)51-29-15-19(9-22(37)31(29)45)13-26(43-49)34(47)40-5-3-16/h1-2,7-11,14-15,44-45,48-49H,3-6,12-13H2,(H,40,47)(H,41,46)/b42-25-,43-26-

Standard InChI Key:  UXXAEQAYQWEARL-ATXSJROWSA-N

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

Properties

Molecular Weight: 1019.13

Molecular Weight (Monoisotopic): 1013.7746

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Masuno MN, Pessah IN, Olmstead MM, Molinski TF..  (2006)  Simplified cyclic analogues of bastadin-5. Structure-activity relationships for modulation of the RyR1/FKBP12 Ca2+ channel complex.,  49  (15): [PMID:16854055] [10.1021/jm050708u]

2. Masuno MN, Molinski TF..  (2003)  Cationic reduction of bastadin-4 to bastadin-5. Preparation of 5-[2h]-bastadin-5 by site-specific isotopic labeling.,  66  (1): [PMID:12542356] [10.1021/np020382h]

3. Pettit GR, Butler MS, Williams MD, Filiatrault MJ, Pettit RK..  (1996)  Isolation and structure of hemibastadinols 1-3 from the Papua New Guinea marine sponge Ianthella basta.,  59  (10): [PMID:8904842] [10.1021/np960249n]

4. Franklin MA, Penn SG, Lebrilla CB, Lam TH, Pessah IN, Molinski TF..  (1996)  Bastadin 20 and bastadin O-sulfate esters from Ianthella basta: novel modulators of the Ry1R FKBP12 receptor complex.,  59  (12): [PMID:8988595] [10.1021/np960507g]

5. 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]

6. 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]

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

8. 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