ID: ALA41177

Max Phase: Preclinical

Molecular Formula: C37H66O7

Molecular Weight: 622.93

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CCCCCC[C@H](O)CCC[C@H](O)[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H](O)CCCCCCCCCCCCC3=C[C@H](C)OC3=O)O2)O1

Standard InChI:  InChI=1S/C37H66O7/c1-3-4-5-15-19-30(38)20-17-22-32(40)34-24-26-36(44-34)35-25-23-33(43-35)31(39)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30-,31+,32-,33+,34+,35+,36+/m0/s1

Standard InChI Key:  DAEFUOXKPZLQMM-AUDZWCKFSA-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: 622.93

Molecular Weight (Monoisotopic): 622.4809

AlogP: 7.86

#Rotatable Bonds: 25

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.39

CX Basic pKa:

CX LogP: 8.68

CX LogD: 8.68

Aromatic Rings: 0

Heavy Atoms: 44

QED Weighted: 0.07

Np Likeness Score: 1.82

References

1. Queiroz EF, Roblot F, Duret P, Figadère B, Gouyette A, Laprévote O, Serani L, Hocquemiller R..  (2000)  Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy.,  43  (8): [PMID:10780917] [10.1021/jm990568m]

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. Gallardo T, Zafra-Polo MC, Tormo JR, González MC, Franck X, Estornell E, Cortes D..  (2000)  Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.,  43  (25): [PMID:11123988] [10.1021/jm000911j]

4. Fall D, Duval RA, Gleye C, Laurens A, Hocquemiller R..  (2004)  Chamuvarinin, an acetogenin bearing a tetrahydropyran ring from the roots of Uvaria chamae.,  67  (6): [PMID:15217292] [10.1021/np030521a]

5. Queiroz EF, Roblot F, Cavé A, Hocquemiller R, Serani L, Laprévote O, Paulo MQ..  (1999)  A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii.,  62  (5): [PMID:10346951] [10.1021/np980482g]

6. Queiroz EF, Roblot F, Figadère B, Laurens A, Duret P, Hocquemiller R, Cavé A, Serani L, Laprévote O, Cotte-Laffitte J, Quéro AM..  (1998)  Three new bistetrahydrofuran acetogenins from the seeds of Annona spinescens.,  61  (1): [PMID:9461649] [10.1021/np9703252]

7. Rupprecht JK, Hui YH, McLaughlin JL..  (1990)  Annonaceous acetogenins: a review.,  53  (2): [PMID:2199608] [10.1021/np50068a001]

8. Guadaño A, Gutiérrez C, de La Peña E, Cortes D, González-Coloma A..  (2000)  Insecticidal and mutagenic evaluation of two annonaceous acetogenins.,  63  (6): [PMID:10869199] [10.1021/np990328+]

9. Yang H, Zhang N, Li X, Chen J, Cai B..  (2009)  Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.,  19  (8): [PMID:19285863] [10.1016/j.bmcl.2009.02.105]

10. OHSAWA K, ATSUZAWA S, MITSUI T, YAMAMOTO I.  (1991)  Isolation and Insecticidal Activity of Three Acetogenins from Seeds of Pond Apple, Annona glabra L.,  16  (1): [10.1584/jpestics.16.93]

11. Shi JF, Wu P, Jiang ZH, Wei XY..  (2014)  Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.,  71  [PMID:24308999] [10.1016/j.ejmech.2013.11.012]

Source

Source(1):

• Scientific Literature