(Z)-Des-methyl-des-amino pateamine A

ID: ALA3126408

Chembl Id: CHEMBL3126408

PubChem CID: 9828287

Max Phase: Preclinical

Molecular Formula: C30H42N2O4S

Molecular Weight: 526.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(/C=C/C(C)=C/[C@@H]1Cc2nc(cs2)CCCCC(=O)O[C@@H](C)C/C(C)=C/C=C\C(=O)O1)=C\CN(C)C

Standard InChI:  InChI=1S/C30H42N2O4S/c1-22(16-17-32(5)6)14-15-24(3)19-27-20-28-31-26(21-37-28)11-7-8-12-29(33)35-25(4)18-23(2)10-9-13-30(34)36-27/h9-10,13-16,19,21,25,27H,7-8,11-12,17-18,20H2,1-6H3/b13-9-,15-14+,22-16+,23-10+,24-19+/t25-,27+/m0/s1

Standard InChI Key:  VSVORQIMRUVRPE-MMPYLIGOSA-N

Alternative Forms

1. Parent:

   

   ALA3126408

   (3S,6Z,8E,11S)-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethylhepta-1,3,5-trienyl]-9,11-dimethyl-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]henicosa-1(21),6,8,18-tetraene-5,13-dione

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: 526.74

Molecular Weight (Monoisotopic): 526.2865

AlogP: 6.16

#Rotatable Bonds: 5

Polar Surface Area: 68.73

Molecular Species: BASE

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.95

CX LogP: 5.84

CX LogD: 4.29

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.34

Np Likeness Score: 1.65

References

1. Low WK, Li J, Zhu M, Kommaraju SS, Shah-Mittal J, Hull K, Liu JO, Romo D..  (2014)  Second-generation derivatives of the eukaryotic translation initiation inhibitor pateamine A targeting eIF4A as potential anticancer agents.,  22  (1): [PMID:24359706] [10.1016/j.bmc.2013.11.046]

Source

Source(1):

• Scientific Literature