{(E)-5-[5-((2E,4E)-2,5-Dimethyl-nona-2,4-dienoyl)-4-hydroxy-6-oxo-6H-pyran-2-yl]-hex-1-enyl}-carbamic acid methyl ester

ID: ALA186014

Chembl Id: CHEMBL186014

Max Phase: Preclinical

Molecular Formula: C24H33NO6

Molecular Weight: 431.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+/-)-Myxopyronin B

Canonical SMILES:  CCCC/C(C)=C/C=C(\C)C(=O)c1c(O)cc(C(C)CC/C=C/NC(=O)OC)oc1=O

Standard InChI:  InChI=1S/C24H33NO6/c1-6-7-10-16(2)12-13-18(4)22(27)21-19(26)15-20(31-23(21)28)17(3)11-8-9-14-25-24(29)30-5/h9,12-15,17,26H,6-8,10-11H2,1-5H3,(H,25,29)/b14-9+,16-12+,18-13+

Standard InChI Key:  SPQDIDVJAZFBRL-NIXSKCKISA-N

Alternative Forms

1. Parent:

   

   ALA186014

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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

Calculated Properties

Molecular Weight: 431.53

Molecular Weight (Monoisotopic): 431.2308

AlogP: 5.36

#Rotatable Bonds: 11

Polar Surface Area: 105.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.86

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 4.59

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 1.27

References

1. Doundoulakis T, Xiang AX, Lira R, Agrios KA, Webber SE, Sisson W, Aust RM, Shah AM, Showalter RE, Appleman JR, Simonsen KB..  (2004)  Myxopyronin B analogs as inhibitors of RNA polymerase, synthesis and biological evaluation.,  14  (22): [PMID:15482944] [10.1016/j.bmcl.2004.08.045]

2. Yakushiji F, Miyamoto Y, Kunoh Y, Okamoto R, Nakaminami H, Yamazaki Y, Noguchi N, Hayashi Y..  (2013)  Novel hybrid-type antimicrobial agents targeting the switch region of bacterial RNA polymerase.,  4  (2): [PMID:24900654] [10.1021/ml300350p]

3. Molodtsov V, Fleming PR, Eyermann CJ, Ferguson AD, Foulk MA, McKinney DC, Masse CE, Buurman ET, Murakami KS..  (2015)  X-ray crystal structures of Escherichia coli RNA polymerase with switch region binding inhibitors enable rational design of squaramides with an improved fraction unbound to human plasma protein.,  58  (7): [PMID:25798859] [10.1021/acs.jmedchem.5b00050]

Source

Source(1):

• Scientific Literature