5-{(R)-2-[(R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid cyclohexylmethyl ester

ID: ALA58625

PubChem CID: 44300808

Max Phase: Preclinical

Molecular Formula: C27H32ClNO7

Molecular Weight: 518.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Cc1ccc2c(c1)OC(C(=O)O)(C(=O)OCC1CCCCC1)O2)NC[C@H](O)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C27H32ClNO7/c1-17(29-15-22(30)20-8-5-9-21(28)14-20)12-19-10-11-23-24(13-19)36-27(35-23,25(31)32)26(33)34-16-18-6-3-2-4-7-18/h5,8-11,13-14,17-18,22,29-30H,2-4,6-7,12,15-16H2,1H3,(H,31,32)/t17-,22+,27?/m1/s1

Standard InChI Key:  KWYXSBDYNQNHBB-VZUMSWISSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA58625

   5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(cyclohexylmethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid

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: 518.01

Molecular Weight (Monoisotopic): 517.1867

AlogP: 4.27

#Rotatable Bonds: 10

Polar Surface Area: 114.32

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.62

CX Basic pKa: 9.59

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.32

Np Likeness Score: -0.19

References

1. Sum FW, Gilbert A, Venkatesan AM, Lim K, Wong V, O'Dell M, Francisco G, Chen Z, Grosu G, Baker J, Ellingboe J, Malamas M, Gunawan I, Primeau J, Largis E, Steiner K..  (1999)  Prodrugs of CL316243: a selective beta3-adrenergic receptor agonist for treating obesity and diabetes.,  9  (14): [PMID:10450954] [10.1016/s0960-894x(99)00316-9]

Source

Source(1):

• Scientific Literature