16-normethyldictyostatin

ID: ALA226932

PubChem CID: 11295339

Max Phase: Preclinical

Molecular Formula: C31H50O6

Molecular Weight: 518.74

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 16-Desmethyldictyostatin | 16-Normethyldictyostatin | 16-Desmethyldictyostatin|16-normethyldictyostatin|CHEMBL226932|(3Z,5E,7R,8S,10S,11Z,13S,14R,15S,20R,21S,22S)-22-[(2S,3Z)-hexa-3,5-dien-2-yl]-8,10,14,20-tetrahydroxy-7,13,15,21-tetramethyl-1-oxacyclodocosa-3,5,11-trien-2-one

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

Standard InChI:  InChI=1S/C31H50O6/c1-7-8-13-24(5)31-25(6)27(33)16-11-9-15-22(3)30(36)23(4)18-19-26(32)20-28(34)21(2)14-10-12-17-29(35)37-31/h7-8,10,12-14,17-19,21-28,30-34,36H,1,9,11,15-16,20H2,2-6H3/b13-8-,14-10+,17-12-,19-18-/t21-,22+,23+,24+,25+,26-,27-,28+,30-,31+/m1/s1

Standard InChI Key:  CRWXTDHKQZZNHK-DIVQDLRVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA226932

   16-Desmethyldictyostatin

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: 518.74

Molecular Weight (Monoisotopic): 518.3607

AlogP: 4.90

#Rotatable Bonds: 3

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.22

CX LogD: 5.22

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.24

Np Likeness Score: 2.52

References

1. 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]

2. Paterson I, Gardner NM, Poullennec KG, Wright AE..  (2007)  Synthesis and biological evaluation of novel analogues of dictyostatin.,  17  (9): [PMID:17336522] [10.1016/j.bmcl.2007.02.031]

3. Paterson I, Gardner NM, Guzmán E, Wright AE..  (2009)  Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.,  17  (6): [PMID:19022679] [10.1016/j.bmc.2008.10.084]

Source

Source(1):

• Scientific Literature