(3R,6R,9R,12S,15S)-6-benzyl-9-((R)-benzyloxy(phenyl)methyl)-3,12-diisobutyl-15-isopropyl-1-methyl-1,4,7,10,13-pentaazacyclopentadecane-2,5,8,11,14-pentaone

ID: ALA2203700

Chembl Id: CHEMBL2203700

PubChem CID: 71457523

Max Phase: Preclinical

Molecular Formula: C43H57N5O6

Molecular Weight: 739.96

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H]1NC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H](CC(C)C)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H]([C@H](OCc2ccccc2)c2ccccc2)NC1=O

Standard InChI:  InChI=1S/C43H57N5O6/c1-27(2)23-33-40(50)47-36(38(32-21-15-10-16-22-32)54-26-31-19-13-9-14-20-31)41(51)44-34(25-30-17-11-8-12-18-30)39(49)46-35(24-28(3)4)43(53)48(7)37(29(5)6)42(52)45-33/h8-22,27-29,33-38H,23-26H2,1-7H3,(H,44,51)(H,45,52)(H,46,49)(H,47,50)/t33-,34+,35+,36+,37-,38+/m0/s1

Standard InChI Key:  HZOKPLKSQDMEIZ-AAQLWUGVSA-N

Alternative Forms

1. Parent:

   

   ALA2203700

   (3R,6R,9R,12S,15S)-6-benzyl-1-methyl-3,12-bis(2-methylpropyl)-9-[(R)-phenyl(phenylmethoxy)methyl]-15-propan-2-yl-1,4,7,10,13-pentazacyclopentadecane-2,5,8,11,14-pentone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 739.96

Molecular Weight (Monoisotopic): 739.4309

AlogP: 4.72

#Rotatable Bonds: 12

Polar Surface Area: 145.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.58

CX Basic pKa: ┄

CX LogP: 5.70

CX LogD: 5.70

Aromatic Rings: 3

Heavy Atoms: 54

QED Weighted: 0.21

Np Likeness Score: 0.75

References

1. Ramsey DM, McConnell JR, Alexander LD, Tanaka KW, Vera CM, McAlpine SR..  (2012)  An Hsp90 modulator that exhibits a unique mechanistic profile.,  22  (9): [PMID:22480433] [10.1016/j.bmcl.2012.03.012]

2. McConnell JR, Alexander LA, McAlpine SR..  (2014)  A heat shock protein 90 inhibitor that modulates the immunophilins and regulates hormone receptors without inducing the heat shock response.,  24  (2): [PMID:24360559] [10.1016/j.bmcl.2013.11.059]

3. McConnell JR, Alexander LA, McAlpine SR..  (2014)  A heat shock protein 90 inhibitor that modulates the immunophilins and regulates hormone receptors without inducing the heat shock response.,  24  (2): [PMID:24360559] [10.1016/j.bmcl.2013.11.059]

4. Koay YC, McConnell JR, Wang Y, Kim SJ, Buckton LK, Mansour F, McAlpine SR..  (2014)  Chemically accessible hsp90 inhibitor that does not induce a heat shock response.,  5  (7): [PMID:25050163] [10.1021/ml500114p]

Source

Source(1):

• Scientific Literature