ID: ALA517037

Max Phase: Preclinical

Molecular Formula: C11H11BrN4O3

Molecular Weight: 327.14

Molecule Type: Small molecule

Representations

Synonyms (2): (-)-Agelastatin A | Agelastatin D
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C1N[C@H]2[C@@H]3NC(=O)c4ccc(Br)n4[C@@H]3C[C@@]2(O)N1

Standard InChI:  InChI=1S/C11H11BrN4O3/c12-6-2-1-4-9(17)13-7-5(16(4)6)3-11(19)8(7)14-10(18)15-11/h1-2,5,7-8,19H,3H2,(H,13,17)(H2,14,15,18)/t5-,7-,8+,11+/m1/s1

Standard InChI Key:  AMKORUFKJJIBRU-GIDNPQMSSA-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: 327.14

Molecular Weight (Monoisotopic): 326.0015

AlogP: -0.32

#Rotatable Bonds: 0

Polar Surface Area: 95.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.51

CX Basic pKa:

CX LogP: -0.54

CX LogD: -0.54

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.53

Np Likeness Score: 2.02

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. Tilvi S, Moriou C, Martin MT, Gallard JF, Sorres J, Patel K, Petek S, Debitus C, Ermolenko L, Al-Mourabit A..  (2010)  Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha.,  73  (4): [PMID:20166736] [10.1021/np900539j]

3. 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