ID: ALA320753

Max Phase: Preclinical

Molecular Formula: C35H64O5

Molecular Weight: 564.89

Molecule Type: Small molecule

Representations

Synonyms (1): Solamin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@H]([C@H](O)CCCCCCCCCCCCC2=C[C@H](C)OC2=O)O1

Standard InChI:  InChI=1S/C35H64O5/c1-3-4-5-6-7-8-12-15-18-21-24-31(36)33-26-27-34(40-33)32(37)25-22-19-16-13-10-9-11-14-17-20-23-30-28-29(2)39-35(30)38/h28-29,31-34,36-37H,3-27H2,1-2H3/t29-,31+,32+,33+,34+/m0/s1

Standard InChI Key:  RBSBTRALZZSVBA-OTUMHNDOSA-N

Molecule Features

Natural Product: Yes

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: 564.89

Molecular Weight (Monoisotopic): 564.4754

AlogP: 9.12

#Rotatable Bonds: 26

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.39

CX Basic pKa:

CX LogP: 10.48

CX LogD: 10.48

Aromatic Rings: 0

Heavy Atoms: 40

QED Weighted: 0.08

Np Likeness Score: 1.65

References

1. Yao ZJ, Wu HP, Wu YL..  (2000)  Polyether mimics of naturally occurring cytotoxic annonaceous acetogenins.,  43  (12): [PMID:10882377] [10.1021/jm990575a]

2. Nakanishi Y, Chang FR, Liaw CC, Wu YC, Bastow KF, Lee KH..  (2003)  Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.,  46  (15): [PMID:12852747] [10.1021/jm020548b]

3. Kojima N, Fushimi T, Maezaki N, Tanaka T, Yamori T..  (2008)  Synthesis of hybrid acetogenins, alpha,beta-unsaturated-gamma-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines.,  18  (5): [PMID:18243700] [10.1016/j.bmcl.2008.01.057]

4. Kojima N, Hayashi H, Suzuki S, Tominaga H, Maezaki N, Tanaka T, Yamori T..  (2008)  Synthesis of C4-fluorinated solamins and their growth inhibitory activity against human cancer cell lines.,  18  (24): [PMID:18993063] [10.1016/j.bmcl.2008.10.069]

5. Chang FR, Wu YC, Duh CY, Wang SK..  (1993)  Studies on the acetogenins of Formosan annonaceous plants. II. Cytotoxic acetogenins from Annona reticulata.,  56  (10): [PMID:8277309] [10.1021/np50100a005]

6. Kojima N, Morioka T, Urabe D, Yano M, Suga Y, Maezaki N, Ohashi-Kobayashi A, Fujimoto Y, Maeda M, Yamori T, Yoshimitsu T, Tanaka T..  (2010)  Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution.,  18  (24): [PMID:21074443] [10.1016/j.bmc.2010.10.004]

7. Kojima N, Suga Y, Hayashi H, Yamori T, Yoshimitsu T, Tanaka T..  (2011)  Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines.,  21  (19): [PMID:21875800] [10.1016/j.bmcl.2011.08.011]

8. Dang QL, Kim WK, Nguyen CM, Choi YH, Choi GJ, Jang KS, Park MS, Lim CH, Luu NH, Kim JC..  (2011)  Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.,  59  (20): [PMID:21910504] [10.1021/jf203017f]

9. Kojima N, Abe M, Suga Y, Ohtsuki K, Tanaka T, Iwasaki H, Yamashita M, Miyoshi H..  (2013)  Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I.,  23  (5): [PMID:23375227] [10.1016/j.bmcl.2013.01.018]

10. Kojima N, Fushimi T, Tatsukawa T, Yoshimitsu T, Tanaka T, Yamori T, Dan S, Iwasaki H, Yamashita M..  (2013)  Structure-activity relationships of hybrid annonaceous acetogenins: powerful growth inhibitory effects of their connecting groups between heterocycle and hydrophobic carbon chain bearing THF ring on human cancer cell lines.,  63  [PMID:23587837] [10.1016/j.ejmech.2013.03.009]

11. Kojima N, Fushimi T, Tatsukawa T, Tanaka T, Okamura M, Akatsuka A, Yamori T, Dan S, Iwasaki H, Yamashita M..  (2014)  Thiophene-3-carboxamide analogue of annonaceous acetogenins as antitumor drug lead.,  86  [PMID:25226228] [10.1016/j.ejmech.2014.09.026]

Source

Source(1):

• Scientific Literature