(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-5-[3-({4-[(10S,11S,14R,15S,17R)-14-ethynyl-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-17-yl]phenyl}(methyl)amino)propoxy]-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

ID: ALA415621

Chembl Id: CHEMBL415621

PubChem CID: 44396251

Max Phase: Preclinical

Molecular Formula: C54H75NO7

Molecular Weight: 850.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(N(C)CCCOC4CC[C@@]5(C)[C@@H](C4)C[C@@H](O)[C@@H]4[C@@H]5C[C@H](O)[C@]5(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@@H]45)cc3)C[C@@]21C

Standard InChI:  InChI=1S/C54H75NO7/c1-7-54(61)24-22-43-40-16-12-34-27-37(56)15-17-39(34)49(40)41(31-52(43,54)4)33-10-13-36(14-11-33)55(6)25-8-26-62-38-21-23-51(3)35(28-38)29-46(57)50-44-19-18-42(32(2)9-20-48(59)60)53(44,5)47(58)30-45(50)51/h1,10-11,13-14,27,32,35,38,40-47,50,57-58,61H,8-9,12,15-26,28-31H2,2-6H3,(H,59,60)/t32-,35+,38?,40+,41-,42-,43+,44+,45+,46-,47+,50+,51+,52+,53-,54+/m1/s1

Standard InChI Key:  AOIBSIQVRJDUOX-RPBDTDFQSA-N

Alternative Forms

1. Parent:

   

   ALA415621

   (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-5-[3-({4-[(10S,11S,14R,15S,17R)-14-ethynyl-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-17-yl]phenyl}(methyl)amino)propoxy]-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0

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: 850.19

Molecular Weight (Monoisotopic): 849.5544

AlogP: 9.26

#Rotatable Bonds: 11

Polar Surface Area: 127.53

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.37

CX Basic pKa: 5.16

CX LogP: 6.35

CX LogD: 4.49

Aromatic Rings: 1

Heavy Atoms: 62

QED Weighted: 0.13

Np Likeness Score: 1.58

References

1. von Geldern TW, Tu N, Kym PR, Link JT, Jae HS, Lai C, Apelqvist T, Rhonnstad P, Hagberg L, Koehler K, Grynfarb M, Goos-Nilsson A, Sandberg J, Osterlund M, Barkhem T, Höglund M, Wang J, Fung S, Wilcox D, Nguyen P, Jakob C, Hutchins C, Färnegårdh M, Kauppi B, Ohman L, Jacobson PB..  (2004)  Liver-selective glucocorticoid antagonists: a novel treatment for type 2 diabetes.,  47  (17): [PMID:15293993] [10.1021/jm0400045]

Source

Source(1):

• Scientific Literature