Riccardi A

ID: ALA475625

Chembl Id: CHEMBL475625

PubChem CID: 14330572

Max Phase: Preclinical

Molecular Formula: C29H26O4

Molecular Weight: 438.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)CCc1ccc(cc1)Oc1cc(ccc1O)CCc1ccc-2c(O)c1

Standard InChI:  InChI=1S/C29H26O4/c1-32-24-12-14-25-22(18-24)9-4-19-5-10-23(11-6-19)33-29-17-21(8-15-27(29)30)3-2-20-7-13-26(25)28(31)16-20/h5-8,10-18,30-31H,2-4,9H2,1H3

Standard InChI Key:  DXBKBLARMLPGND-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA475625

   RICCARDIN A

Molecule Features

Natural Product: Yes

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: 438.52

Molecular Weight (Monoisotopic): 438.1831

AlogP: 6.45

#Rotatable Bonds: 1

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 7.46

CX LogD: 7.44

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: 1.54

References

1. Hioki H, Shima N, Kawaguchi K, Harada K, Kubo M, Esumi T, Nishimaki-Mogami T, Sawada J, Hashimoto T, Asakawa Y, Fukuyama Y..  (2009)  Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRalpha agonists.,  19  (3): [PMID:19103488] [10.1016/j.bmcl.2008.12.022]

2. Harinantenaina L, Quang DN, Takeshi N, Hashimoto T, Kohchi C, Soma G, Asakawa Y..  (2005)  Bis(bibenzyls) from liverworts inhibit lipopolysaccharide-induced inducible NOS in RAW 264.7 cells: a study of structure-activity relationships and molecular mechanism.,  68  (12): [PMID:16378374] [10.1021/np0502589]

3. Morita H, Zaima K, Koga I, Saito A, Tamamoto H, Okazaki H, Kaneda T, Hashimoto T, Asakawa Y..  (2011)  Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts.,  19  (13): [PMID:21652215] [10.1016/j.bmc.2011.05.019]

4. Iwai Y, Murakami K, Gomi Y, Hashimoto T, Asakawa Y, Okuno Y, Ishikawa T, Hatakeyama D, Echigo N, Kuzuhara T..  (2011)  Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.,  6  (5): [PMID:21625478] [10.1371/journal.pone.0019825]

5. Asakawa Y, Ludwiczuk A..  (2018)  Chemical Constituents of Bryophytes: Structures and Biological Activity.,  81  (3): [PMID:29019405] [10.1021/acs.jnatprod.6b01046]

Source

Source(1):

• Scientific Literature