ID: ALA464946

Max Phase: Preclinical

Molecular Formula: C28H45N3O5

Molecular Weight: 503.68

Molecule Type: Small molecule

Representations

Synonyms (2): (4R,5R)-Antillatoxin | Antillatoxin
Synonyms from Alternative Forms(2):

Canonical SMILES:  C=C1CC(=O)N[C@@H](C)C(=O)N(C)[C@@H](C(C)C)C(=O)NCC(=O)O[C@@H](/C(C)=C/C(C)=C/C(C)(C)C)[C@@H]1C

Standard InChI:  InChI=1S/C28H45N3O5/c1-16(2)24-26(34)29-15-23(33)36-25(19(5)12-17(3)14-28(8,9)10)20(6)18(4)13-22(32)30-21(7)27(35)31(24)11/h12,14,16,20-21,24-25H,4,13,15H2,1-3,5-11H3,(H,29,34)(H,30,32)/b17-14+,19-12+/t20-,21+,24+,25+/m1/s1

Standard InChI Key:  WNMROEVYEZDXEL-OITYILOZSA-N

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

Properties

Molecular Weight: 503.68

Molecular Weight (Monoisotopic): 503.3359

AlogP: 3.54

#Rotatable Bonds: 3

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.15

CX Basic pKa:

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 0

Heavy Atoms: 36

QED Weighted: 0.35

Np Likeness Score: 1.91

References

1. Li WI, Marquez BL, Okino T, Yokokawa F, Shioiri T, Gerwick WH, Murray TF..  (2004)  Characterization of the preferred stereochemistry for the neuropharmacologic actions of antillatoxin.,  67  (4): [PMID:15104484] [10.1021/np0303409]

2. Li WI, Marquez BL, Okino T, Yokokawa F, Shioiri T, Gerwick WH, Murray TF..  (2004)  Characterization of the preferred stereochemistry for the neuropharmacologic actions of antillatoxin.,  67  (4): [PMID:15104484] [10.1021/np0303409]

3. Nogle LM, Okino T, Gerwick WH..  (2001)  Antillatoxin B, a neurotoxic lipopeptide from the marine cyanobacterium Lyngbya majuscula.,  64  (7): [PMID:11473443] [10.1021/np010107f]

4. Orjala J, Gerwick WH..  (1996)  Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula.,  59  (4): [PMID:8699186] [10.1021/np960085a]

5. de Lera Ruiz M, Kraus RL..  (2015)  Voltage-Gated Sodium Channels: Structure, Function, Pharmacology, and Clinical Indications.,  58  (18): [PMID:25927480] [10.1021/jm501981g]

6. Mehrotra S, Pierce ML, Cao Z, Jabba SV, Gerwick WH, Murray TF..  (2022)  Antillatoxin-Stimulated Neurite Outgrowth Involves the Brain-Derived Neurotrophic Factor (BDNF) - Tropomyosin Related Kinase B (TrkB) Signaling Pathway.,  85  (3.0): [PMID:35239341] [10.1021/acs.jnatprod.1c01001]

7. Xu J, Zhang T, Yao J, Lu J, Liu Z, Ding L..  (2020)  Recent advances in chemistry and bioactivity of marine cyanobacteria Moorea species.,  201  [PMID:32652435] [10.1016/j.ejmech.2020.112473]

Source

Source(1):

• Scientific Literature