5-(3,5-dibromo-4-hydroxybenzylidene)-4-(3,5-dibromo-4-hydroxyphenyl)furan-2(5H)-one

ID: ALA511842

Chembl Id: CHEMBL511842

PubChem CID: 6055630

Max Phase: Preclinical

Molecular Formula: C17H8Br4O4

Molecular Weight: 595.86

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rubrolide A | Rubrolide A|CHEMBL511842|SCHEMBL12402314|BDBM50064292|NSC701303|NSC-701303|(5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]furan-2-one

Canonical SMILES:  O=C1C=C(c2cc(Br)c(O)c(Br)c2)/C(=C/c2cc(Br)c(O)c(Br)c2)O1

Standard InChI:  InChI=1S/C17H8Br4O4/c18-10-1-7(2-11(19)16(10)23)3-14-9(6-15(22)25-14)8-4-12(20)17(24)13(21)5-8/h1-6,23-24H/b14-3-

Standard InChI Key:  RQFYDYMMVXKTBY-BNNQUZSASA-N

Alternative Forms

1. Parent:

   

   ALA511842

   RUBROLIDE 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: 595.86

Molecular Weight (Monoisotopic): 591.7156

AlogP: 6.13

#Rotatable Bonds: 2

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 6.34

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: 1.04

References

1. Manzanaro S, Salva J, de la Fuente JA..  (2006)  Phenolic marine natural products as aldose reductase inhibitors.,  69  (10): [PMID:17067167] [10.1021/np0503698]

2. Wang W, Kim H, Nam SJ, Rho BJ, Kang H..  (2012)  Antibacterial butenolides from the Korean tunicate Pseudodistoma antinboja.,  75  (12): [PMID:23145884] [10.1021/np300544a]

3. Thorson MK, Van Wagoner RM, Harper MK, Ireland CM, Majtan T, Kraus JP, Barrios AM..  (2015)  Marine natural products as inhibitors of cystathionine beta-synthase activity.,  25  (5): [PMID:25666819] [10.1016/j.bmcl.2015.01.013]

4. Bae J, Cho E, Park JS, Won TH, Seo SY, Oh DC, Oh KB, Shin J..  (2020)  Isocadiolides A-H: Polybrominated Aromatics from a Synoicum sp. Ascidian.,  83  (2): [PMID:31967465] [10.1021/acs.jnatprod.9b00968]

5. Bracegirdle J, Stevenson LJ, Sharrock AV, Page MJ, Vorster JA, Owen JG, Ackerley DF, Keyzers RA..  (2021)  Hydrated Rubrolides from the New Zealand Tunicate Synoicum kuranui.,  84  (2.0): [PMID:33496582] [10.1021/acs.jnatprod.0c01248]

Source

Source(1):

• Scientific Literature