3-Chloro-5-[(E)-7-((S)-5,5-dimethyl-4-oxo-tetrahydro-furan-2-yl)-3-methyl-octa-2,6-dienyl]-4,6-dihydroxy-2-methyl-benzaldehyde

ID: ALA133046

Cas Number: 38462-04-3

PubChem CID: 6434242

Max Phase: Preclinical

Molecular Formula: C23H29ClO5

Molecular Weight: 420.93

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ascofuranone | Ascofuranone|38462-04-3|Ascofuranon|(-)-ascofuranone|5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde|I31EFB9515|(S)-ascofuranone|SCHEMBL639391|UNII-I31EFB9515|CHEMBL133046|DTXSID60903967|CHEBI:156148|VGYPZLGWVQQOST-JUERRSSISA-N|BDBM50459778|Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl)-, (S-(E,E))-|Q4803989|(S-(E,E))-3-chloro-4,6-dihydroxy-Show More⌵

Canonical SMILES:  C/C(=C\Cc1c(O)c(Cl)c(C)c(C=O)c1O)CC/C=C(\C)[C@@H]1CC(=O)C(C)(C)O1

Standard InChI:  InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1

Standard InChI Key:  VGYPZLGWVQQOST-JUERRSSISA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    6.2350  -15.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8096  -15.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223  -15.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2392  -16.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223  -16.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8096  -16.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0408  -16.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8452  -16.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9533  -15.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2578  -15.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7035  -15.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9477  -15.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2363  -15.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6645  -15.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969  -15.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0789  -15.7751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3773  -15.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5237  -15.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223  -17.6798    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0969  -14.3747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5182  -14.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519  -16.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8069  -15.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928  -16.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5579  -16.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6243  -17.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0942  -15.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2322  -14.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3773  -14.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9491  -14.7665    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  5  1  0
  7  9  1  0
  8  7  1  0
  9 13  1  0
 10 11  1  0
 11  9  1  0
 12  1  1  0
 13 18  2  0
 14 12  1  0
 15  2  1  0
 16 10  2  0
 17 14  2  0
 18 23  1  0
 19  5  1  0
 20 15  2  0
 21  3  1  0
 22  4  1  0
 23 27  1  0
 24  6  1  0
 25  8  1  0
 26  8  1  0
 27 17  1  0
 28 13  1  0
 29 17  1  0
  9 30  1  1
  6  2  2  0
 10  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA133046

   ASCOFURANONE

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: 420.93

Molecular Weight (Monoisotopic): 420.1704

AlogP: 5.22

#Rotatable Bonds: 7

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.84

CX Basic pKa: ┄

CX LogP: 6.40

CX LogD: 4.92

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 1.94

References

1. Togashi M, Ozawa S, Abe S, Nishimura T, Tsuruga M, Ando K, Tamura G, Kuwahara S, Ubukata M, Magae J..  (2003)  Ascochlorin derivatives as ligands for nuclear hormone receptors.,  46  (19): [PMID:12954063] [10.1021/jm0205649]

2. Zhang P, Bao B, Dang HT, Hong J, Lee HJ, Yoo ES, Bae KS, Jung JH..  (2009)  Anti-inflammatory sesquiterpenoids from a sponge-derived Fungus Acremonium sp.,  72  (2): [PMID:19199645] [10.1021/np8006793]

3. Watts KR, Ratnam J, Ang KH, Tenney K, Compton JE, McKerrow J, Crews P..  (2010)  Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.,  18  (7): [PMID:20303767] [10.1016/j.bmc.2010.02.034]

4. Meco-Navas A, Ebiloma GU, Martín-Domínguez A, Martínez-Benayas I, Cueto-Díaz EJ, Alhejely AS, Balogun EO, Saito M, Matsui M, Arai N, Shiba T, Harada S, de Koning HP, Dardonville C..  (2018)  SAR of 4-Alkoxybenzoic Acid Inhibitors of the Trypanosome Alternative Oxidase.,  9  (9): [PMID:30258542] [10.1021/acsmedchemlett.8b00282]

5. Ebiloma GU, Ayuga TD, Balogun EO, Gil LA, Donachie A, Kaiser M, Herraiz T, Inaoka DK, Shiba T, Harada S, Kita K, de Koning HP, Dardonville C..  (2018)  Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense.,  150  [PMID:29544150] [10.1016/j.ejmech.2018.02.075]

6. West RA, O'Doherty OG, Askwith T, Atack J, Beswick P, Laverick J, Paradowski M, Pennicott LE, Rao SPS, Williams G, Ward SE..  (2017)  African trypanosomiasis: Synthesis & SAR enabling novel drug discovery of ubiquinol mimics for trypanosome alternative oxidase.,  141  [PMID:29107420] [10.1016/j.ejmech.2017.09.067]

7. Hao X, Li S, Ni J, Wang G, Li F, Li Q, Chen S, Shu J, Gan M..  (2021)  Acremopeptaibols A-F, 16-Residue Peptaibols from the Sponge-Derived Acremonium sp. IMB18-086 Cultivated with Heat-Killed Pseudomonas aeruginosa.,  84  (11.0): [PMID:34781681] [10.1021/acs.jnatprod.1c00834]

8. Luo X, Cai G, Guo Y, Gao C, Huang W, Zhang Z, Lu H, Liu K, Chen J, Xiong X, Lei J, Zhou X, Wang J, Liu Y..  (2021)  Exploring Marine-Derived Ascochlorins as Novel Human Dihydroorotate Dehydrogenase Inhibitors for Treatment of Triple-Negative Breast Cancer.,  64  (18.0): [PMID:34516133] [10.1021/acs.jmedchem.1c01402]

9. Cisneros D, Cueto-Díaz EJ, Medina-Gil T, Chevillard R, Bernal-Fraile T, López-Sastre R, Aldfer MM, Ungogo MA, Elati HAA, Arai N, Otani M, Matsushiro S, Kojima C, Ebiloma GU, Shiba T, de Koning HP, Dardonville C..  (2022)  Imidazoline- and Benzamidine-Based Trypanosome Alternative Oxidase Inhibitors: Synthesis and Structure-Activity Relationship Studies.,  13  (2.0): [PMID:35178188] [10.1021/acsmedchemlett.1c00717]

10. Yuan S, Gopal JV, Ren S, Chen L, Liu L, Gao Z..  (2020)  Anticancer fungal natural products: Mechanisms of action and biosynthesis.,  202  [PMID:32652407] [10.1016/j.ejmech.2020.112502]

Source

Source(1):

• Scientific Literature