ID: ALA2017441

Max Phase: Preclinical

Molecular Formula: C36H50N2O7

Molecular Weight: 622.80

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CO[C@H]1/C=C/C=C/C=C/C[C@H](OC(=O)[C@@H](C)NC(=O)C2CCCCC2)[C@H](C)[C@@H](O)/C(C)=C\CCc2cc(O)cc(c2)NC(=O)C1

Standard InChI:  InChI=1S/C36H50N2O7/c1-24-14-13-15-27-20-29(22-30(39)21-27)38-33(40)23-31(44-4)18-11-6-5-7-12-19-32(25(2)34(24)41)45-36(43)26(3)37-35(42)28-16-9-8-10-17-28/h5-7,11-12,14,18,20-22,25-26,28,31-32,34,39,41H,8-10,13,15-17,19,23H2,1-4H3,(H,37,42)(H,38,40)/b6-5+,12-7+,18-11+,24-14-/t25-,26+,31-,32-,34-/m0/s1

Standard InChI Key:  WACCDLYIHBADOZ-KOPFIVEKSA-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: 622.80

Molecular Weight (Monoisotopic): 622.3618

AlogP: 5.68

#Rotatable Bonds: 5

Polar Surface Area: 134.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.32

CX Basic pKa:

CX LogP: 5.61

CX LogD: 5.60

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.25

Np Likeness Score: 1.32

References

1. Brandt GE, Blagg BS..  (2011)  Monoenomycin: A Simplified Trienomycin A Analogue that Manifests Anticancer Activity.,  2  (10): [PMID:22162786] [10.1021/ml200108y]

2. Tang D, Liu LL, He QR, Yan W, Li D, Gao JM..  (2018)  Ansamycins with Antiproliferative and Antineuroinflammatory Activity from Moss-Soil-Derived Streptomyces cacaoi subsp. asoensis H2S5.,  81  (9): [PMID:30132670] [10.1021/acs.jnatprod.8b00203]

3. Luo YQ, Bian ZY, Xu DD, Tang JJ, Gao JM..  (2023)  Trienomycin A-simplified analogs: Synthesis and anti-neuroinflammatory activity.,  80  [PMID:36592870] [10.1016/j.bmcl.2022.129122]

4. Yang X, Wu W, Li H, Zhang M, Chu Z, Wang X, Sun P..  (2022)  Natural occurrence, bioactivity, and biosynthesis of triene-ansamycins.,  244  [PMID:36240545] [10.1016/j.ejmech.2022.114815]

Source

Source(1):

• Scientific Literature