4-[4-(2-Nitro-vinyl)-phenoxysulfonyl]-benzoic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA505705

Chembl Id: CHEMBL505705

PubChem CID: 14862530

Max Phase: Preclinical

Molecular Formula: C25H22N6O10S

Molecular Weight: 598.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COC(=O)c2ccc(S(=O)(=O)Oc3ccc(/C=C/[N+](=O)[O-])cc3)cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C25H22N6O10S/c26-22-19-23(28-12-27-22)30(13-29-19)24-21(33)20(32)18(40-24)11-39-25(34)15-3-7-17(8-4-15)42(37,38)41-16-5-1-14(2-6-16)9-10-31(35)36/h1-10,12-13,18,20-21,24,32-33H,11H2,(H2,26,27,28)/b10-9+/t18-,20-,21-,24-/m1/s1

Standard InChI Key:  UHYWUEAMUOPMRO-YSKCLZGSSA-N

Alternative Forms

1. Parent:

   

   ALA505705

   [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-[4-[(E)-2-nitroethenyl]phenoxy]sulfonylbenzoate

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: 598.55

Molecular Weight (Monoisotopic): 598.1118

AlogP: 0.90

#Rotatable Bonds: 9

Polar Surface Area: 232.12

Molecular Species: NEUTRAL

HBA: 15

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.46

CX Basic pKa: 3.94

CX LogP: 1.78

CX LogD: 1.78

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.11

Np Likeness Score: 0.35

References

1. Traxler PM, Wacker O, Bach HL, Geissler JF, Kump W, Meyer T, Regenass U, Roesel JL, Lydon N..  (1991)  Sulfonylbenzoyl-nitrostyrenes: potential bisubstrate type inhibitors of the EGF-receptor tyrosine protein kinase.,  34  (8): [PMID:1652014] [10.1021/jm00112a003]

2. Chang CJ, Geahlen RL..  (1992)  Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents.,  55  (11): [PMID:1479375] [10.1021/np50089a001]

Source

Source(1):

• Scientific Literature