Cyclosporin O

ID: ALA5183632

Chembl Id: CHEMBL5183632

PubChem CID: 11170764

Max Phase: Preclinical

Molecular Formula: C60H109N11O11

Molecular Weight: 1160.60

Names and Identifiers

Canonical SMILES:  CCC[C@@H]1NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O

Standard InChI:  InChI=1S/C60H109N11O11/c1-25-26-42-56(78)65(18)32-48(72)66(19)43(27-33(2)3)54(76)64-49(38(12)13)59(81)67(20)44(28-34(4)5)52(74)61-40(16)51(73)62-41(17)55(77)69(22)46(30-36(8)9)57(79)70(23)47(31-37(10)11)58(80)71(24)50(39(14)15)60(82)68(21)45(29-35(6)7)53(75)63-42/h33-47,49-50H,25-32H2,1-24H3,(H,61,74)(H,62,73)(H,63,75)(H,64,76)/t40-,41+,42-,43-,44-,45-,46-,47-,49-,50-/m0/s1

Standard InChI Key:  NLGBWFHSHJPDQX-DTKOGYIOSA-N

Alternative Forms

1. Parent:

   

   ALA5183632

   cyclo[Ala-D-Ala-N(Me)Leu-N(Me)Leu-N(Me)Val-N(Me)Leu-Nva-Sar-N(Me)Leu-Val-N(Me)Leu]

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1160.60

Molecular Weight (Monoisotopic): 1159.8308

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. Lee D, Kang JA, Lim C, Bae S, Choi J, Park M, Kim YC, Cho Y, Park SG, Seo J..  (2022)  Entry inhibition of hepatitis B virus using cyclosporin O derivatives with peptoid side chain incorporation.,  68  [PMID:35691131] [10.1016/j.bmc.2022.116862]

2. Lee D, Lee S, Choi J, Song YK, Kim MJ, Shin DS, Bae MA, Kim YC, Park CJ, Lee KR, Choi JH, Seo J..  (2021)  Interplay among Conformation, Intramolecular Hydrogen Bonds, and Chameleonicity in the Membrane Permeability and Cyclophilin A Binding of Macrocyclic Peptide Cyclosporin O Derivatives.,  64  (12.0): [PMID:34096287] [10.1021/acs.jmedchem.1c00211]

Source

Source(1):

• Scientific Literature