4-hydroxy-6-((2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dienyl)-3-methyl-5-propylpyridin-2(1H)-one

ID: ALA269802

Chembl Id: CHEMBL269802

PubChem CID: 54696388

Max Phase: Preclinical

Molecular Formula: C19H29NO3

Molecular Weight: 319.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: iromycin B | IROMYCIN B|CHEMBL269802|MEGxm0_000380|ACon0_000665|CHEBI:203468|BDBM50411914|2-hydroxy-6-[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dienyl]-3-methyl-5-propyl-1H-pyridin-4-one

Canonical SMILES:  CCCc1c(C/C=C(\C)C/C=C/C(C)(C)O)[nH]c(=O)c(C)c1O

Standard InChI:  InChI=1S/C19H29NO3/c1-6-8-15-16(20-18(22)14(3)17(15)21)11-10-13(2)9-7-12-19(4,5)23/h7,10,12,23H,6,8-9,11H2,1-5H3,(H2,20,21,22)/b12-7+,13-10+

Standard InChI Key:  ZCSULNWARAXOGW-IZENVRNYSA-N

Alternative Forms

1. Parent:

   

   ALA269802

   IROMYCIN B

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: 319.44

Molecular Weight (Monoisotopic): 319.2147

AlogP: 3.55

#Rotatable Bonds: 7

Polar Surface Area: 73.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.55

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.67

Np Likeness Score: 1.80

References

1. Surup F, Shojaei H, von Zezschwitz P, Kunze B, Grond S..  (2008)  Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.,  16  (4): [PMID:18054490] [10.1016/j.bmc.2007.11.023]

Source

Source(1):

• Scientific Literature