5'-Deoxy-5'-[3-(7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)propyl]thio-adenosine

ID: ALA4789060

Chembl Id: CHEMBL4789060

PubChem CID: 162670268

Max Phase: Preclinical

Molecular Formula: C23H28N8O6S

Molecular Weight: 544.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CSCCCNC(=O)C2Cc3ccc([N+](=O)[O-])cc3CN2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C23H28N8O6S/c24-20-17-21(28-10-27-20)30(11-29-17)23-19(33)18(32)16(37-23)9-38-5-1-4-25-22(34)15-7-12-2-3-14(31(35)36)6-13(12)8-26-15/h2-3,6,10-11,15-16,18-19,23,26,32-33H,1,4-5,7-9H2,(H,25,34)(H2,24,27,28)/t15?,16-,18-,19-,23-/m1/s1

Standard InChI Key:  UPRXYLMCECRARE-RRBMSBAWSA-N

Alternative Forms

1. Parent:

   

   ALA4789060

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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: 544.59

Molecular Weight (Monoisotopic): 544.1853

AlogP: -0.11

#Rotatable Bonds: 9

Polar Surface Area: 203.58

Molecular Species: NEUTRAL

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.47

CX Basic pKa: 7.08

CX LogP: -0.21

CX LogD: -0.38

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.14

Np Likeness Score: -0.12

References

1. Lu J,Bart AG,Wu Q,Criscione KR,McLeish MJ,Scott EE,Grunewald GL.  (2020)  Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine N-Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains.,  63  (22): [PMID:33147410] [10.1021/acs.jmedchem.0c01475]

Source

Source(1):

• Scientific Literature