cis-Isopropyl-(L-valyl)-L-serin-O3-yl Ester 9-{[(5S)-2-Hydroxy-2-oxido-1,4,2-dioxaphosphinan-5-yl]methyl}-2,6-diaminopurine

ID: ALA1257400

PubChem CID: 52946203

Max Phase: Preclinical

Molecular Formula: C20H33N8O7P

Molecular Weight: 528.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@@H](CO[P@@]1(=O)CO[C@@H](Cn2cnc3c(N)nc(N)nc32)CO1)NC(=O)[C@@H](N)C(C)C

Standard InChI:  InChI=1S/C20H33N8O7P/c1-10(2)14(21)18(29)25-13(19(30)35-11(3)4)7-34-36(31)9-32-12(6-33-36)5-28-8-24-15-16(22)26-20(23)27-17(15)28/h8,10-14H,5-7,9,21H2,1-4H3,(H,25,29)(H4,22,23,26,27)/t12-,13+,14-,36+/m0/s1

Standard InChI Key:  DUNXKVFMHGQXKD-ZHZZNDMPSA-N

Molfile:  

     RDKit          2D

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   12.1162   -8.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8752   -9.1440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0502   -9.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6342   -9.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6414   -8.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8092   -9.8480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0429  -10.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 12 13  1  0
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  1  2  2  0
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  3  4  2  0
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  4  6  1  0
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  5  6  2  0
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  6  7  1  0
 26 29  1  0
  7  8  2  0
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  8  9  1  0
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  9  5  1  0
 23 32  2  0
  9 10  1  0
 23 33  1  0
 11 10  1  1
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 11 12  1  0
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 11 16  1  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1257400

   propan-2-yl (2R)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-[[(2S,5S)-5-[(2,6-diaminopurin-9-yl)methyl]-2-oxo-1,4,2lambda5-dioxaphosphinan-2-yl]oxy]propanoate

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: 528.51

Molecular Weight (Monoisotopic): 528.2210

AlogP: -0.01

#Rotatable Bonds: 10

Polar Surface Area: 221.82

Molecular Species: BASE

HBA: 14

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.00

CX Basic pKa: 8.51

CX LogP: -0.55

CX LogD: -1.71

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.24

Np Likeness Score: -0.15

References

1. Krecmerová M, Holý A, Andrei G, Pomeisl K, Tichý T, Brehová P, Masojídková M, Dracínský M, Pohl R, Laflamme G, Naesens L, Hui H, Cihlar T, Neyts J, De Clercq E, Balzarini J, Snoeck R..  (2010)  Synthesis of ester prodrugs of 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as anti-poxvirus agents.,  53  (19): [PMID:20809641] [10.1021/jm901828c]

Source

Source(1):

• Scientific Literature