Phosphoric acid (S)-2-amino-3-(1H-imidazol-4-yl)-propyl ester (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA1160242

Chembl Id: CHEMBL1160242

PubChem CID: 44298295

Max Phase: Preclinical

Molecular Formula: C16H23N8O7P

Molecular Weight: 470.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OC[C@@H](N)Cc2c[nH]cn2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H23N8O7P/c17-8(1-9-2-19-5-20-9)3-29-32(27,28)30-4-10-12(25)13(26)16(31-10)24-7-23-11-14(18)21-6-22-15(11)24/h2,5-8,10,12-13,16,25-26H,1,3-4,17H2,(H,19,20)(H,27,28)(H2,18,21,22)/t8-,10+,12+,13+,16+/m0/s1

Standard InChI Key:  SBCKMBGGZNSZKS-TXRSOIPOSA-N

Alternative Forms

1. Parent:

   

   ALA1160242

   [(2S)-2-amino-3-(1H-imidazol-5-yl)propyl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate

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: 470.38

Molecular Weight (Monoisotopic): 470.1427

AlogP: -1.55

#Rotatable Bonds: 9

Polar Surface Area: 229.77

Molecular Species: ZWITTERION

HBA: 13

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.85

CX Basic pKa: 9.65

CX LogP: -3.67

CX LogD: -3.68

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: 1.08

References

1. Forrest AK, Jarvest RL, Mensah LM, O'Hanlon PJ, Pope AJ, Sheppard RJ..  (2000)  Aminoalkyl adenylate and aminoacyl sulfamate intermediate analogues differing greatly in affinity for their cognate Staphylococcus aureus aminoacyl tRNA synthetases.,  10  (16): [PMID:10969988] [10.1016/s0960-894x(00)00360-7]

Source

Source(1):

• Scientific Literature