ID: ALA188704

Max Phase: Preclinical

Molecular Formula: C32H53NO8

Molecular Weight: 579.78

Molecule Type: Small molecule

Representations

Synonyms (1): 14-Normethyldiscodermolide
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C/C=C\[C@H](C)[C@H](OC(N)=O)[C@@H](C)[C@H](O)[C@@H](C)C/C=C\[C@H](C)[C@@H](O)[C@@H](C)/C=C\[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C

Standard InChI:  InChI=1S/C32H53NO8/c1-9-10-12-21(5)30(41-32(33)39)23(7)28(36)19(3)14-11-13-18(2)27(35)20(4)15-16-25(34)17-26-22(6)29(37)24(8)31(38)40-26/h9-13,15-16,18-30,34-37H,1,14,17H2,2-8H3,(H2,33,39)/b12-10-,13-11-,16-15-/t18-,19-,20-,21-,22-,23-,24+,25+,26-,27+,28+,29-,30-/m0/s1

Standard InChI Key:  YQHRYTPPOURLFW-BYMFUPSWSA-N

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

Properties

Molecular Weight: 579.78

Molecular Weight (Monoisotopic): 579.3771

AlogP: 3.91

#Rotatable Bonds: 16

Polar Surface Area: 159.54

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 0

Heavy Atoms: 41

QED Weighted: 0.10

Np Likeness Score: 2.59

References

1. Smith AB, Freeze BS, LaMarche MJ, Sager J, Kinzler KW, Vogelstein B..  (2005)  Discodermolide analogues as the chemical component of combination bacteriolytic therapy.,  15  (15): [PMID:15979874] [10.1016/j.bmcl.2005.05.068]

2. Jung WH, Harrison C, Shin Y, Fournier JH, Balachandran R, Raccor BS, Sikorski RP, Vogt A, Curran DP, Day BW..  (2007)  Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.,  50  (13): [PMID:17542572] [10.1021/jm061385k]

Source

Source(1):

• Scientific Literature