ID: ALA511731

Max Phase: Preclinical

Molecular Formula: C26H29N3O5

Molecular Weight: 463.53

Molecule Type: Small molecule

Representations

Synonyms (1): Sclerotiamide
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC1(C)C=Cc2c(ccc3c2NC(=O)[C@@]32[C@H](O)[C@@]34NC(=O)[C@]5(CCCN5C3=O)C[C@H]4C2(C)C)O1

Standard InChI:  InChI=1S/C26H29N3O5/c1-22(2)10-8-13-15(34-22)7-6-14-17(13)27-20(32)25(14)18(30)26-16(23(25,3)4)12-24(19(31)28-26)9-5-11-29(24)21(26)33/h6-8,10,16,18,30H,5,9,11-12H2,1-4H3,(H,27,32)(H,28,31)/t16-,18-,24-,25-,26+/m0/s1

Standard InChI Key:  CFJMAERFDLWMJL-LQKPOZSPSA-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: 463.53

Molecular Weight (Monoisotopic): 463.2107

AlogP: 1.71

#Rotatable Bonds: 0

Polar Surface Area: 107.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.25

CX Basic pKa:

CX LogP: 1.12

CX LogD: 1.12

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.54

Np Likeness Score: 2.29

References

1. Whyte AC, Gloer JB, Wicklow DT, Dowdw PF..  (1996)  Sclerotiamide: a new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum.,  59  (11): [PMID:8946752] [10.1021/np960607m]

2. Wang X, You J, King JB, Powell DR, Cichewicz RH..  (2012)  Waikialoid A suppresses hyphal morphogenesis and inhibits biofilm development in pathogenic Candida albicans.,  75  (4): [PMID:22400916] [10.1021/np2009994]

3. Peng J, Zhang XY, Tu ZC, Xu XY, Qi SH..  (2013)  Alkaloids from the deep-sea-derived fungus Aspergillus westerdijkiae DFFSCS013.,  76  (5): [PMID:23701598] [10.1021/np400132m]

4. Lavey NP, Coker JA, Ruben EA, Duerfeldt AS..  (2016)  Sclerotiamide: The First Non-Peptide-Based Natural Product Activator of Bacterial Caseinolytic Protease P.,  79  (4): [PMID:26967980] [10.1021/acs.jnatprod.5b01091]

Source

Source(1):

• Scientific Literature