(R)-2,4,6-Trimethyl-deca-2,4-dienoic acid {(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-6-(2-hydroxy-5-oxo-cyclopent-1-enylcarbamoyl)-hexa-1,3,5-trienyl]-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl}-amide

ID: ALA285848

Chembl Id: CHEMBL285848

Max Phase: Preclinical

Molecular Formula: C31H38N2O7

Molecular Weight: 550.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@@H](C)/C=C(C)/C=C(\C)C(=O)NC1=C[C@@](O)(/C=C/C=C/C=C/C(=O)NC2=C(O)CCC2=O)[C@@H]2O[C@@H]2C1=O

Standard InChI:  InChI=1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28-,29-,31+/m1/s1

Standard InChI Key:  TWWQHCKLTXDWBD-MVTGTTCWSA-N

Alternative Forms

1. Parent:

   

   ALA285848

   MANUMYCIN A

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: 550.65

Molecular Weight (Monoisotopic): 550.2679

AlogP: 3.70

#Rotatable Bonds: 12

Polar Surface Area: 145.33

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.04

CX Basic pKa:

CX LogP: 3.06

CX LogD: 3.05

Aromatic Rings: 0

Heavy Atoms: 40

QED Weighted: 0.16

Np Likeness Score: 1.81

References

1. Hamasaki A, Naka H, Tamanoi F, Umezawa K, Otsuka M..  (2003)  A novel metal-chelating inhibitor of protein farnesyltransferase.,  13  (9): [PMID:12699746] [10.1016/s0960-894x(03)00183-5]

2. Li F, Maskey RP, Qin S, Sattler I, Fiebig HH, Maier A, Zeeck A, Laatsch H..  (2005)  Chinikomycins A and B: isolation, structure elucidation, and biological activity of novel antibiotics from a marine Streptomyces sp. isolate M045.,  68  (3): [PMID:15787434] [10.1021/np030518r]

3. PubChem BioAssay data set, 

4. Tuladhar A, Rein KS..  (2018)  Manumycin A Is a Potent Inhibitor of Mammalian Thioredoxin Reductase-1 (TrxR-1).,  9  (4): [PMID:29670693] [10.1021/acsmedchemlett.7b00489]

5. Korzeniecki C, Priefer R..  (2021)  Targeting KRAS mutant cancers by preventing signaling transduction in the MAPK pathway.,  211  [PMID:33228976] [10.1016/j.ejmech.2020.113006]

6. Gendaszewska-Darmach E, Garstka MA, Błażewska KM..  (2021)  Targeting Small GTPases and Their Prenylation in Diabetes Mellitus.,  64  (14.0): [PMID:34236862] [10.1021/acs.jmedchem.1c00410]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays