elisabatin A

ID: ALA494655

Chembl Id: CHEMBL494655

PubChem CID: 397069

Max Phase: Preclinical

Molecular Formula: C20H22O3

Molecular Weight: 310.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=C[C@@H]1C[C@H](C)c2c(O)cc(C)c3c2C1=C(C)C(=O)C3=O

Standard InChI:  InChI=1S/C20H22O3/c1-9(2)6-13-7-10(3)15-14(21)8-11(4)16-18(15)17(13)12(5)19(22)20(16)23/h6,8,10,13,21H,7H2,1-5H3/t10-,13+/m0/s1

Standard InChI Key:  JVQJPMIBFYBOEO-GXFFZTMASA-N

Alternative Forms

1. Parent:

   

   ALA494655

   ELISABATIN 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: 310.39

Molecular Weight (Monoisotopic): 310.1569

AlogP: 4.33

#Rotatable Bonds: 1

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.03

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 4.86

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: 2.08

References

1. Rodríguez AD, Ramírez C, Rodríguez II..  (1999)  Elisabatins A and B: new amphilectane-type diterpenes from the West Indian sea whip Pseudopterogorgia elisabethae.,  62  (7): [PMID:10425124] [10.1021/np990090p]

2. PubChem BioAssay data set, 

3. Tillotson J, Kedzior M, Guimarães L, Ross AB, Peters TL, Ambrose AJ, Schmidlin CJ, Zhang DD, Costa-Lotufo LV, Rodríguez AD, Schatz JH, Chapman E..  (2017)  ATP-competitive, marine derived natural products that target the DEAD box helicase, eIF4A.,  27  (17): [PMID:28757063] [10.1016/j.bmcl.2017.07.045]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays