(R)-2,5-Diamino-6-[5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-hexanoic acid (episinefungin)

ID: ALA2093043

Chembl Id: CHEMBL2093043

PubChem CID: 12771338

Max Phase: Preclinical

Molecular Formula: C15H23N7O5

Molecular Weight: 381.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](C[C@H](N)CC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7+,8-,10-,11-,14-/m1/s1

Standard InChI Key:  LMXOHSDXUQEUSF-RZBSXSLJSA-N

Alternative Forms

1. Parent:

   

   ALA2093043

   (2S,5R)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid

Molecule Features

Natural Product: Yes

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: 381.39

Molecular Weight (Monoisotopic): 381.1761

AlogP: -2.06

#Rotatable Bonds: 7

Polar Surface Area: 208.65

Molecular Species: ZWITTERION

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.64

CX Basic pKa: 10.07

CX LogP: -5.14

CX LogD: -6.85

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.31

Np Likeness Score: 1.25

References

1. Barton DH, Géro SD, Lawrence F, Robert-Gero M, Quiclet-Sire B, Samadi M..  (1992)  Total synthesis of uracil analogues of sinefungin.,  35  (1): [PMID:1732534] [10.1021/jm00079a007]

Source

Source(1):

• Scientific Literature