dictyostatin

ID: ALA226880

PubChem CID: 11353099

Max Phase: Preclinical

Molecular Formula: C32H52O6

Molecular Weight: 532.76

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dictyostatin | dictyostatin|(-)-dictyostatin|CHEMBL226880|SCHEMBL14094924|Q43297542|(3~{z},5~{e},7~{r},8~{s},10~{s},11~{z},13~{s},14~{r},15~{s},17~{s},20~{r},21~{s},22~{s})-22-[(2~{s},3~{z})-Hexa-3,5-Dien-2-Yl]-7,13,15,17,21-Pentamethyl-8,10,14,20-Tetrakis(Oxidanyl)-1-Oxacyclodocosa-3,5,11-Trien-2-One|(3Z,5E,7R,8S,10S,11Z,13S,14R,15S,17S,20R,21S,22S)-22-[(2S,3Z)-hexa-3,5-dien-2-yl]-8,10,14,20-tetrahydroxy-7,13,15,17,21-pentamethyl-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)C[C@@H](C)CC[C@@H](O)[C@@H]1C

Standard InChI:  InChI=1S/C32H52O6/c1-8-9-12-24(5)32-26(7)28(34)18-15-21(2)19-25(6)31(37)23(4)16-17-27(33)20-29(35)22(3)13-10-11-14-30(36)38-32/h8-14,16-17,21-29,31-35,37H,1,15,18-20H2,2-7H3/b12-9-,13-10+,14-11-,17-16-/t21-,22+,23-,24-,25-,26-,27+,28+,29-,31-,32-/m0/s1

Standard InChI Key:  OFPZNTXZCGKCMU-VXBOPZJTSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA226880

   DICTYOSTATIN

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: 532.76

Molecular Weight (Monoisotopic): 532.3764

AlogP: 5.14

#Rotatable Bonds: 3

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.51

CX LogD: 5.51

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.23

Np Likeness Score: 2.59

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, Poullennec KG, Wright AE..  (2008)  Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.,  71  (3): [PMID:18081257] [10.1021/np070547s]

4. Paterson I, Gardner NM, Guzmán E, Wright AE..  (2008)  Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.,  18  (23): [PMID:18951787] [10.1016/j.bmcl.2008.09.109]

5. 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]

6. Brunden KR, Gardner NM, James MJ, Yao Y, Trojanowski JQ, Lee VM, Paterson I, Ballatore C, Smith AB..  (2013)  MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.,  4  (9): [PMID:24900764] [10.1021/ml400233e]

Source

Source(1):

• Scientific Literature