ID: ALA451275

Max Phase: Preclinical

Molecular Formula: C12H13BrN4O4

Molecular Weight: 357.16

Molecule Type: Small molecule

Representations

Synonyms (1): (-)-Agelastatin C
Synonyms from Alternative Forms(1):

Canonical SMILES:  CN1C(=O)N[C@@]2(O)[C@@H]3NC(=O)c4ccc(Br)n4[C@@H]3C[C@@]12O

Standard InChI:  InChI=1S/C12H13BrN4O4/c1-16-10(19)15-12(21)8-6(4-11(12,16)20)17-5(9(18)14-8)2-3-7(17)13/h2-3,6,8,20-21H,4H2,1H3,(H,14,18)(H,15,19)/t6-,8-,11+,12-/m1/s1

Standard InChI Key:  FTXCKDLRLVUKQU-RMEKTUJTSA-N

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

Properties

Molecular Weight: 357.16

Molecular Weight (Monoisotopic): 356.0120

AlogP: -0.66

#Rotatable Bonds: 0

Polar Surface Area: 106.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.87

CX Basic pKa:

CX LogP: -0.51

CX LogD: -0.51

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.49

Np Likeness Score: 1.87

References

1. Hong TW, Jímenez DR, Molinski TF..  (1998)  Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A.,  61  (1): [PMID:9461668] [10.1021/np9703813]

2. Stout EP, Choi MY, Castro JE, Molinski TF..  (2014)  Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies.,  57  (12): [PMID:24673739] [10.1021/jm4016922]

Source

Source(1):

• Scientific Literature