ID: ALA1628277

Max Phase: Preclinical

Molecular Formula: C38H67NO10

Molecular Weight: 697.95

Molecule Type: Small molecule

Representations

Synonyms (1): ABT-229
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)C[C@@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)CC)[C@H]2O)[C@@]2(C)CC(C)=C(O2)[C@H](C)[C@@H](O)[C@H]1C

Standard InChI:  InChI=1S/C38H67NO10/c1-14-28-23(6)30(40)24(7)32-20(3)17-38(11,49-32)34(48-36-31(41)27(39(12)15-2)16-21(4)45-36)25(8)33(26(9)35(42)46-28)47-29-19-37(10,43-13)18-22(5)44-29/h21-31,33-34,36,40-41H,14-19H2,1-13H3/t21-,22-,23+,24-,25+,26-,27+,28-,29+,30+,31-,33+,34-,36+,37+,38-/m1/s1

Standard InChI Key:  IWTSXJNGTTXMFK-DLKZTDGISA-N

Molecule Features

Natural Product: Yes

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: 697.95

Molecular Weight (Monoisotopic): 697.4765

AlogP: 5.20

#Rotatable Bonds: 8

Polar Surface Area: 125.38

Molecular Species: BASE

HBA: 11

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.82

CX Basic pKa: 9.35

CX LogP: 4.56

CX LogD: 2.62

Aromatic Rings: 0

Heavy Atoms: 49

QED Weighted: 0.33

Np Likeness Score: 1.46

References

1. Li JJ, Chao HG, Wang H, Tino JA, Lawrence RM, Ewing WR, Ma Z, Yan M, Slusarchyk D, Seethala R, Sun H, Li D, Burford NT, Stoffel RH, Salyan ME, Li CY, Witkus M, Zhao N, Rich A, Gordon DA..  (2004)  Discovery of a potent and novel motilin agonist.,  47  (7): [PMID:15027861] [10.1021/jm0304865]

2. Shaw SJ, Chen Y, Zheng H, Fu H, Burlingame MA, Marquez S, Li Y, Claypool M, Carreras CW, Crumb W, Hardy DJ, Myles DC, Liu Y..  (2009)  Structure-activity relationships of 9-substituted-9-dihydroerythromycin-based motilin agonists: optimizing for potency and safety.,  52  (21): [PMID:19821563] [10.1021/jm901107f]

3. Liu Y, Li Y, Chen Y, Zheng H, Claypool M, Myles DC, Carreras CW..  (2010)  9-Dihydroerythromycins as non-antibiotic motilin receptor agonists.,  20  (19): [PMID:20801039] [10.1016/j.bmcl.2010.08.030]

4. Liu Y, Li Y, Myles DC, Claypool M, Carreras CW, Shaw SJ..  (2010)  9-Dihydroerythromycin ethers as motilin agonists--developing structure-activity relationships for potency and safety.,  18  (21): [PMID:20869254] [10.1016/j.bmc.2010.08.035]

5. Liu Y, Carreras CW, Claypool M, Myles DC, Shaw SJ..  (2011)  The role of the 4''-hydroxyl on motilin agonist potency in the 9-dihydroerythromycin series.,  21  (12): [PMID:21570844] [10.1016/j.bmcl.2011.04.078]

Source

Source(1):

• Scientific Literature