(R)-2-amino-2-methyl-4-(1-methyl-5-(4-p-tolylbutanoyl)-1H-pyrrol-2-yl)butyl dihydrogen phosphate

ID: ALA1951588

Chembl Id: CHEMBL1951588

Cas Number: 840523-39-9

PubChem CID: 11676168

Max Phase: Preclinical

Molecular Formula: C21H31N2O5P

Molecular Weight: 422.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CCCC(=O)c2ccc(CC[C@@](C)(N)COP(=O)(O)O)n2C)cc1

Standard InChI:  InChI=1S/C21H31N2O5P/c1-16-7-9-17(10-8-16)5-4-6-20(24)19-12-11-18(23(19)3)13-14-21(2,22)15-28-29(25,26)27/h7-12H,4-6,13-15,22H2,1-3H3,(H2,25,26,27)/t21-/m1/s1

Standard InChI Key:  SFFJDCSCTWIGSG-OAQYLSRUSA-N

Alternative Forms

1. Parent:

   

   ALA1951588

   1-Butanone, 1-(5-((3R)-3-amino-3-methyl-4-(phosphonooxy)butyl)-1-methyl-1H-pyrrol-2-yl)-4-(4-methylphenyl)-

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: 422.46

Molecular Weight (Monoisotopic): 422.1971

AlogP: 3.30

#Rotatable Bonds: 11

Polar Surface Area: 114.78

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.69

CX Basic pKa: 10.18

CX LogP: 2.13

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: 0.00

References

1. Nishi T, Miyazaki S, Takemoto T, Suzuki K, Iio Y, Nakajima K, Ohnuki T, Kawase Y, Nara F, Inaba S, Izumi T, Yuita H, Oshima K, Doi H, Inoue R, Tomisato W, Kagari T, Shimozato T..  (2011)  Discovery of CS-0777: A Potent, Selective, and Orally Active S1P1 Agonist.,  2  (5): [PMID:24900318] [10.1021/ml100301k]

2. Nakamura T, Asano M, Sekiguchi Y, Mizuno Y, Tamaki K, Nara F, Kawase Y, Yabe Y, Nakai D, Kamiyama E, Urasaki-Kaneno Y, Shimozato T, Doi-Komuro H, Kagari T, Tomisato W, Inoue R, Nagasaki M, Yuita H, Oguchi-Oshima K, Kaneko R, Nishi T..  (2012)  Synthesis and evaluation of CS-2100, a potent, orally active and S1P(3)- sparing S1P(1) agonist.,  51  [PMID:22405291] [10.1016/j.ejmech.2012.02.022]

Source

Source(1):

• Scientific Literature