({{{[(R)-1-(6-Amino-9H-purin-9-yl)propan-2-yl]oxy}methyl}phosphoryl}bis(oxy))bis(propane-3,1-diyl)(2S,2'S,3S,3'S)-bis(2-amino-3-methylpentanoate)hydrochloride

ID: ALA4475750

PubChem CID: 155537957

Max Phase: Preclinical

Molecular Formula: C27H49ClN7O8P

Molecular Weight: 629.70

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](N)C(=O)OCCCOP(=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)OCCCOC(=O)[C@@H](N)[C@@H](C)CC.Cl

Standard InChI:  InChI=1S/C27H48N7O8P.ClH/c1-6-18(3)21(28)26(35)38-10-8-12-41-43(37,42-13-9-11-39-27(36)22(29)19(4)7-2)17-40-20(5)14-34-16-33-23-24(30)31-15-32-25(23)34;/h15-16,18-22H,6-14,17,28-29H2,1-5H3,(H2,30,31,32);1H/t18-,19-,20+,21-,22-;/m0./s1

Standard InChI Key:  KUBZEEPOBFFAQG-FUULQFTFSA-N

Molfile:  

     RDKit          2D

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   23.9454  -26.1347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.1810  -24.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8964  -24.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8967  -25.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.7773  -31.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6600  -26.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4204  -26.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2496  -27.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.3392  -31.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
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  8 14  1  0
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 16 17  1  0
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 18  3  1  0
  3 19  1  0
 19 20  1  0
 16 21  1  6
  4 22  1  0
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 20 25  1  0
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 24 27  1  0
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 30 31  1  1
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 38 39  1  1
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 37 41  1  6
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 38 43  1  0
 43 44  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 629.70

Molecular Weight (Monoisotopic): 629.3302

AlogP: 2.61

#Rotatable Bonds: 21

Polar Surface Area: 219.02

Molecular Species: NEUTRAL

HBA: 15

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 7.77

CX LogP: 1.38

CX LogD: 0.70

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.10

Np Likeness Score: -0.04

References

1. Wang A, Wu S, Tao Z, Li X, Lv K, Ma C, Li Y, Li L, Liu M..  (2019)  Design, Synthesis, and Anti-HBV Activity of New Bis(l-amino acid) Ester Tenofovir Prodrugs.,  10  (6): [PMID:31223460] [10.1021/acsmedchemlett.9b00184]

Source

Source(1):

• Scientific Literature