ID: ALA455487

Max Phase: Preclinical

Molecular Formula: C34H25Br5N4O8

Molecular Weight: 1017.11

Molecule Type: Small molecule

Representations

Synonyms (2): Bastadin 4 | Bastadin-4
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C1N/C=C/c2ccc(c(Br)c2)Oc2cc(cc(Br)c2O)CCNC(=O)/C(=N/O)Cc2cc(Br)c(c(Br)c2)Oc2cc(cc(Br)c2O)C/C1=N\O

Standard InChI:  InChI=1S/C34H25Br5N4O8/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/h1-3,5,7-11,14-15,44-45,48-49H,4,6,12-13H2,(H,40,47)(H,41,46)/b5-3+,42-25+,43-26+

Standard InChI Key:  YCBNAUHIFJRIQW-XDDRAWHZSA-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: 1017.11

Molecular Weight (Monoisotopic): 1011.7589

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, 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]

2. 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]

3. Miao SC, Andersen RJ, Allen TM..  (1990)  Cytotoxic metabolites from the sponge Ianthella basta collected in Papua New Guinea.,  53  (6): [PMID:2089117] [10.1021/np50072a007]

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

6. 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