ID: ALA1093304

Max Phase: Preclinical

Molecular Formula: C34H44ClF2N3O2

Molecular Weight: 600.19

Molecule Type: Small molecule

Representations

Synonyms (1): MK-0489
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)[C@@H]3CN(C(C)(C)C)C[C@H]3c3ccc(F)cc3F)CC2)c2cc(Cl)c(C)cc21

Standard InChI:  InChI=1S/C34H44ClF2N3O2/c1-20-14-24-27(16-29(20)35)34(17-28(24)33(6,7)38-21(2)41)10-12-39(13-11-34)31(42)26-19-40(32(3,4)5)18-25(26)23-9-8-22(36)15-30(23)37/h8-9,14-16,25-26,28H,10-13,17-19H2,1-7H3,(H,38,41)/t25-,26+,28+/m0/s1

Standard InChI Key:  KMNARKQYUZICHM-ZRRKCSAHSA-N

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

Properties

Molecular Weight: 600.19

Molecular Weight (Monoisotopic): 599.3090

AlogP: 6.70

#Rotatable Bonds: 4

Polar Surface Area: 52.65

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 9.05

CX LogP: 5.53

CX LogD: 3.88

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.43

Np Likeness Score: -0.68

References

1. He S, Ye Z, Dobbelaar PH, Sebhat IK, Guo L, Liu J, Jian T, Lai Y, Franklin CL, Bakshi RK, Dellureficio JP, Hong Q, Tsou NN, Ball RG, Cashen DE, Martin WJ, Weinberg DH, Macneil T, Tang R, Tamvakopoulos C, Peng Q, Miller RR, Stearns RA, Chen HY, Chen AS, Strack AM, Fong TM, Macintyre DE, Wyvratt MJ, Nargund RP..  (2010)  Discovery of a spiroindane based compound as a potent, selective, orally bioavailable melanocortin subtype-4 receptor agonist.,  20  (7): [PMID:20207541] [10.1016/j.bmcl.2010.02.058]

2. He S, Ye Z, Dobbelaar PH, Sebhat IK, Guo L, Liu J, Jian T, Lai Y, Franklin CL, Bakshi RK, Dellureficio JP, Hong Q, Weinberg DH, Macneil T, Tang R, Strack AM, Tamvakopoulos C, Peng Q, Miller RR, Stearns RA, Chen HY, Chen AS, Fong TM, Wyvratt MJ, Nargund RP..  (2010)  Spiroindane based amides as potent and selective MC4R agonists for the treatment of obesity.,  20  (15): [PMID:20598882] [10.1016/j.bmcl.2010.06.062]

Source

Source(1):

• Scientific Literature