(2'R,3'S,7'S,10'S,E)-4-Hydroxy-10'-isopropyl-2',7'-dimethylspiro[cyclohexane-1,13'-11-oxa-3,8-diaza-1(2,7)-quinolina-5(3,1)-pyridazinacyclopentadecaphanen]-14'-ene-4',6',9',12'-tetraone

ID: ALA4161280

Chembl Id: CHEMBL4161280

PubChem CID: 90307125

Max Phase: Preclinical

Molecular Formula: C33H43N5O6

Molecular Weight: 605.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1OC(=O)C2(/C=C/c3ccc4ccc(nc4c3)[C@@H](C)NC(=O)[C@@H]3CCCN(N3)C(=O)[C@H](C)NC1=O)CCC(O)CC2

Standard InChI:  InChI=1S/C33H43N5O6/c1-19(2)28-30(41)35-21(4)31(42)38-17-5-6-26(37-38)29(40)34-20(3)25-10-9-23-8-7-22(18-27(23)36-25)11-14-33(32(43)44-28)15-12-24(39)13-16-33/h7-11,14,18-21,24,26,28,37,39H,5-6,12-13,15-17H2,1-4H3,(H,34,40)(H,35,41)/b14-11+/t20-,21+,24?,26+,28+,33?/m1/s1

Standard InChI Key:  LVSYXHXWHDMBGO-ZKGIKYJASA-N

Alternative Forms

1. Parent:

   

   ALA4161280

   (2R,5S,11S,14S,18E)-4'-hydroxy-2,11-dimethyl-14-propan-2-ylspiro[15-oxa-3,9,12,26,29-pentazatetracyclo[18.5.3.15,9.023,27]nonacosa-1(26),18,20(28),21,23(27),24-hexaene-17,1'-cyclohexane]-4,10,13,16-tetrone

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: 605.74

Molecular Weight (Monoisotopic): 605.3213

AlogP: 2.93

#Rotatable Bonds: 1

Polar Surface Area: 149.96

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.16

CX Basic pKa: 3.50

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.36

Np Likeness Score: 0.95

References

1. Mackman RL, Steadman VA, Dean DK, Jansa P, Poullennec KG, Appleby T, Austin C, Blakemore CA, Cai R, Cannizzaro C, Chin G, Chiva JC, Dunbar NA, Fliri H, Highton AJ, Hui H, Ji M, Jin H, Karki K, Keats AJ, Lazarides L, Lee YJ, Liclican A, Mish M, Murray B, Pettit SB, Pyun P, Sangi M, Santos R, Sanvoisin J, Schmitz U, Schrier A, Siegel D, Sperandio D, Stepan G, Tian Y, Watt GM, Yang H, Schultz BE..  (2018)  Discovery of a Potent and Orally Bioavailable Cyclophilin Inhibitor Derived from the Sanglifehrin Macrocycle.,  61  (21): [PMID:30074795] [10.1021/acs.jmedchem.8b00802]

2. Mackman RL, Steadman VA, Dean DK, Jansa P, Poullennec KG, Appleby T, Austin C, Blakemore CA, Cai R, Cannizzaro C, Chin G, Chiva JC, Dunbar NA, Fliri H, Highton AJ, Hui H, Ji M, Jin H, Karki K, Keats AJ, Lazarides L, Lee YJ, Liclican A, Mish M, Murray B, Pettit SB, Pyun P, Sangi M, Santos R, Sanvoisin J, Schmitz U, Schrier A, Siegel D, Sperandio D, Stepan G, Tian Y, Watt GM, Yang H, Schultz BE..  (2018)  Discovery of a Potent and Orally Bioavailable Cyclophilin Inhibitor Derived from the Sanglifehrin Macrocycle.,  61  (21): [PMID:30074795] [10.1021/acs.jmedchem.8b00802]

Source

Source(1):

• Scientific Literature