ID: ALA1802135

Max Phase: Preclinical

Molecular Formula: C22H23N3O3

Molecular Weight: 377.44

Molecule Type: Small molecule

Representations

Synonyms (1): Protuboxepin A
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCC(C)[C@@H]1NC(=O)[C@@H](Cc2ccccc2)n2c1nc1c(c2=O)C=CC=CO1

Standard InChI:  InChI=1S/C22H23N3O3/c1-3-14(2)18-19-24-21-16(11-7-8-12-28-21)22(27)25(19)17(20(26)23-18)13-15-9-5-4-6-10-15/h4-12,14,17-18H,3,13H2,1-2H3,(H,23,26)/t14?,17-,18+/m1/s1

Standard InChI Key:  UOBOWSHNMYJJFQ-QIWLAUOQSA-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: 377.44

Molecular Weight (Monoisotopic): 377.1739

AlogP: 3.16

#Rotatable Bonds: 4

Polar Surface Area: 73.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.64

CX Basic pKa:

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.89

Np Likeness Score: 1.63

References

1. Lee SU, Asami Y, Lee D, Jang JH, Ahn JS, Oh H..  (2011)  Protuboxepins A and B and protubonines A and B from the marine-derived fungus Aspergillus sp. SF-5044.,  74  (5): [PMID:21366228] [10.1021/np100880b]

2. Asami Y, Jang JH, Soung NK, He L, Moon DO, Kim JW, Oh H, Muroi M, Osada H, Kim BY, Ahn JS..  (2012)  Protuboxepin A, a marine fungal metabolite, inducing metaphase arrest and chromosomal misalignment in tumor cells.,  20  (12): [PMID:22595423] [10.1016/j.bmc.2012.04.039]

Source

Source(1):

• Scientific Literature