bisorbicillinol

ID: ALA518705

Chembl Id: CHEMBL518705

PubChem CID: 11375385

Max Phase: Preclinical

Molecular Formula: C28H32O8

Molecular Weight: 496.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bisorbicillinol | bisorbicillinol|CHEMBL518705|(1R,2S,6S,7S,8S,9S,12Z)-2-[(2E,4E)-hexa-2,4-dienoyl]-5,6,9-trihydroxy-12-[(2E,4E)-1-hydroxyhexa-2,4-dienylidene]-1,4,6,9-tetramethyltricyclo[6.2.2.02,7]dodec-4-ene-3,10,11-trione

Canonical SMILES:  C/C=C/C=C/C(=O)[C@]12C(=O)C(C)=C(O)[C@@](C)(O)[C@H]1[C@H]1/C(=C(O)\C=C\C=C\C)C(=O)[C@]2(C)C(=O)[C@@]1(C)O

Standard InChI:  InChI=1S/C28H32O8/c1-7-9-11-13-16(29)18-19-20-27(6,36)21(31)15(3)22(32)28(20,17(30)14-12-10-8-2)25(4,23(18)33)24(34)26(19,5)35/h7-14,19-20,29,31,35-36H,1-6H3/b9-7+,10-8+,13-11+,14-12+,18-16-/t19-,20-,25-,26+,27+,28-/m1/s1

Standard InChI Key:  VNCFIIWODJHVEC-NEBBRQRBSA-N

Alternative Forms

1. Parent:

   

   ALA518705

   BISORBICILLINOL

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: 496.56

Molecular Weight (Monoisotopic): 496.2097

AlogP: 2.94

#Rotatable Bonds: 5

Polar Surface Area: 149.20

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.59

CX Basic pKa:

CX LogP: 3.28

CX LogD: -0.07

Aromatic Rings: 0

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: 1.97

References

1. Maskey RP, Grün-Wollny I, Laatsch H..  (2005)  Sorbicillin analogues and related dimeric compounds from Penicillium notatum.,  68  (6): [PMID:15974609] [10.1021/np040137t]

2. Sugaya K, Terajima T, Takahashi A, Onose JI, Abe N..  (2019)  Bisorbicillinol inhibits Lyn tyrosine kinase for allergic response on RBL-2H3 cells.,  29  (6): [PMID:30711393] [10.1016/j.bmcl.2019.01.019]

Source

Source(1):

• Scientific Literature