5-((E)-2-Bromo-vinyl)-1-{4-hydroxy-5-[5-(2-methoxy-2-phenylsulfanyl-ethyl)-3-methyl-2-oxo-2lambda*5*-[1,3,2]oxazaphospholidin-2-yloxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

ID: ALA3142385

PubChem CID: 90662941

Max Phase: Preclinical

Molecular Formula: C23H29BrN3O8PS

Molecular Weight: 618.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(CC1CN(C)P(=O)(OC[C@H]2O[C@@H](n3cc(/C=C/Br)c(=O)[nH]c3=O)C[C@@H]2O)O1)Sc1ccccc1

Standard InChI:  InChI=1S/C23H29BrN3O8PS/c1-26-13-16(10-21(32-2)37-17-6-4-3-5-7-17)35-36(26,31)33-14-19-18(28)11-20(34-19)27-12-15(8-9-24)22(29)25-23(27)30/h3-9,12,16,18-21,28H,10-11,13-14H2,1-2H3,(H,25,29,30)/b9-8+/t16?,18-,19+,20+,21?,36?/m0/s1

Standard InChI Key:  VBPAEHGBIIHYHA-QCCOKTQRSA-N

Molfile:  

     RDKit          2D

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   -2.0363    1.7176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1385    1.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8734   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1305    2.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4239    1.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8762    0.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227   -2.8840    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2950   -0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812   -1.5643    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -3.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5239    0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -2.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -3.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3818   -3.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -5.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5311   -4.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0161   -5.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 15  1  0
  3  1  1  0
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  5  1  1  1
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 35 33  2  0
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 37 35  1  0
  4  8  1  0
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 37 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3142385

   5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-[[5-(2-methoxy-2-phenylsulfanylethyl)-3-methyl-2-oxo-1,3,2lambda5-oxazaphospholidin-2-yl]oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione

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: 618.44

Molecular Weight (Monoisotopic): 617.0596

AlogP: 3.16

#Rotatable Bonds: 10

Polar Surface Area: 132.32

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.23

Np Likeness Score: 0.28

References

1. Kumar A, Coe PL, Jones AS, Walker RT, Balzarini J, De Clercq E..  (1990)  Synthesis and biological evaluation of some cyclic phosphoramidate nucleoside derivatives.,  33  (9): [PMID:2391680] [10.1021/jm00171a009]

Source

Source(1):

• Scientific Literature