(2S,4R)-1-((4E,6E)-(2S,3S,8S,9S)-3-Acetylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoyl)-pyrrolidine-2,4-dicarboxylic acid

ID: ALA100033

Chembl Id: CHEMBL100033

PubChem CID: 44330221

Max Phase: Preclinical

Molecular Formula: C28H38N2O7

Molecular Weight: 514.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H](Cc1ccccc1)[C@@H](C)/C=C(C)/C=C/[C@H](NC(C)=O)[C@H](C)C(=O)N1C[C@H](C(=O)O)C[C@H]1C(=O)O

Standard InChI:  InChI=1S/C28H38N2O7/c1-17(13-18(2)25(37-5)14-21-9-7-6-8-10-21)11-12-23(29-20(4)31)19(3)26(32)30-16-22(27(33)34)15-24(30)28(35)36/h6-13,18-19,22-25H,14-16H2,1-5H3,(H,29,31)(H,33,34)(H,35,36)/b12-11+,17-13+/t18-,19-,22+,23-,24-,25-/m0/s1

Standard InChI Key:  MRISQXIQFOEPLQ-MCHVOXOFSA-N

Alternative Forms

1. Parent:

   

   ALA100033

   (2S,4R)-1-((4E,6E)-(2S,3S,8S,9S)-3-Acetylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoyl)-pyrrolidine-2,4-dicarboxylic acid

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: 514.62

Molecular Weight (Monoisotopic): 514.2679

AlogP: 2.91

#Rotatable Bonds: 12

Polar Surface Area: 133.24

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.48

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: -3.85

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.37

Np Likeness Score: 0.77

References

1. Gulledge BM, Aggen JB, Eng H, Sweimeh K, Chamberlin AR..  (2003)  Microcystin analogues comprised only of Adda and a single additional amino acid retain moderate activity as PP1/PP2A inhibitors.,  13  (17): [PMID:14611855] [10.1016/s0960-894x(03)00588-2]

Source

Source(1):

• Scientific Literature