Cyclosporin A derivative

ID: ALA264029

Chembl Id: CHEMBL264029

PubChem CID: 44293331

Max Phase: Preclinical

Molecular Formula: C62H109N11O13

Molecular Weight: 1216.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H]1NC(=O)[C@H]([C@@H]2OC(C(C)=O)C[C@H]2C)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/C62H109N11O13/c1-25-42-58(81)67(18)31-48(75)68(19)43(26-32(2)3)55(78)66-49(36(10)11)61(84)69(20)44(27-33(4)5)54(77)63-39(15)53(76)64-40(16)57(80)70(21)45(28-34(6)7)59(82)71(22)46(29-35(8)9)60(83)72(23)50(37(12)13)62(85)73(24)51(56(79)65-42)52-38(14)30-47(86-52)41(17)74/h32-40,42-47,49-52H,25-31H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/t38-,39+,40-,42+,43+,44+,45+,46+,47?,49+,50+,51+,52-/m1/s1

Standard InChI Key:  ISAWPVUEDPNXKH-FGAWDVMJSA-N

Alternative Forms

1. Parent:

   

   ALA264029

   (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(2R,3R)-5-acetyl-3-methyloxolan-2-yl]-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,2

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: 1216.62

Molecular Weight (Monoisotopic): 1215.8206

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. Eberle MK, Jutzi-Eme A, Nuninger F.  (1995)  Modifications of the MeBmt side chain of cyclosporin A,  5  (15): [10.1016/0960-894X(95)00281-W]

2. Liu Y,Ruan H,Li Y,Sun G,Liu X,He W,Mao F,He M,Yan L,Zhong G,Yan H,Li W,Zhang Z.  (2021)  Potent and Specific Inhibition of NTCP-Mediated HBV/HDV Infection and Substrate Transporting by a Novel, Oral-Available Cyclosporine A Analogue.,  64  (1.0): [PMID:33369415] [10.1021/acs.jmedchem.0c01484]

Source

Source(1):

• Scientific Literature