(13E,15E)-(3S,6S,9R,10R,11S,12S,21S)-3-(3-Hydroxy-benzyl)-6-isopropyl-10,12-dimethoxy-9,11-dimethyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

ID: ALA4090107

PubChem CID: 67978739

Max Phase: Preclinical

Molecular Formula: C34H50N4O8

Molecular Weight: 642.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1[C@@H](C)[C@@H](OC)/C=C/C=C/CCOC(=O)[C@@H]2CCCN(N2)C(=O)[C@H](Cc2cccc(O)c2)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1C

Standard InChI:  InChI=1S/C34H50N4O8/c1-21(2)29-32(41)35-27(20-24-13-11-14-25(39)19-24)33(42)38-17-12-15-26(37-38)34(43)46-18-10-8-7-9-16-28(44-5)22(3)30(45-6)23(4)31(40)36-29/h7-9,11,13-14,16,19,21-23,26-30,37,39H,10,12,15,17-18,20H2,1-6H3,(H,35,41)(H,36,40)/b8-7+,16-9+/t22-,23+,26-,27-,28-,29-,30+/m0/s1

Standard InChI Key:  NEMOPOKMUVPNPN-JJMZVKDLSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4090107

   3-[(3-Hydroxyphenyl)methyl]-10,12-Dimethoxy-9,11-Dimethyl-6-(Propan-2-Yl)-19-Oxa-1,4,7,25-Tetraazabicyclo[19.3.1]pentacosa-13,15-Diene-2,5,8,20-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: 642.79

Molecular Weight (Monoisotopic): 642.3629

AlogP: 2.42

#Rotatable Bonds: 5

Polar Surface Area: 155.53

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.46

CX Basic pKa: 0.82

CX LogP: 2.92

CX LogD: 2.91

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.35

Np Likeness Score: 1.52

References

1. Steadman VA, Pettit SB, Poullennec KG, Lazarides L, Keats AJ, Dean DK, Stanway SJ, Austin CA, Sanvoisin JA, Watt GM, Fliri HG, Liclican AC, Jin D, Wong MH, Leavitt SA, Lee YJ, Tian Y, Frey CR, Appleby TC, Schmitz U, Jansa P, Mackman RL, Schultz BE..  (2017)  Discovery of Potent Cyclophilin Inhibitors Based on the Structural Simplification of Sanglifehrin A.,  60  (3): [PMID:28075591] [10.1021/acs.jmedchem.6b01329]

Source

Source(1):

• Scientific Literature