ID: ALA280487

Max Phase: Preclinical

Molecular Formula: C44H68O13

Molecular Weight: 805.02

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=C1[C@@H](O)[C@@H]2O[C@]3(CC[C@H](/C=C/[C@@H](C)[C@@H]4CC(C)=C[C@@]5(O[C@H](C[C@@](C)(O)C(=O)O)CC[C@H]5O)O4)O3)CC[C@H]2O[C@@H]1[C@@H](O)C[C@H](C)[C@H]1O[C@@]2(CCCCO2)CC[C@H]1C

Standard InChI:  InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1

Standard InChI Key:  QNDVLZJODHBUFM-WFXQOWMNSA-N

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

Properties

Molecular Weight: 805.02

Molecular Weight (Monoisotopic): 804.4660

AlogP: 5.21

#Rotatable Bonds: 10

Polar Surface Area: 182.83

Molecular Species: ACID

HBA: 12

HBD: 5

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.76

CX Basic pKa:

CX LogP: 5.13

CX LogD: 1.86

Aromatic Rings: 0

Heavy Atoms: 57

QED Weighted: 0.18

Np Likeness Score: 1.82

References

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2. Quinn RJ, Taylor C, Suganuma M, Fujiki H.  (1993)  The conserved acid binding domain model of inhibitors of protein phosphatases 1 and 2A: Molecular modelling aspects.,  3  (6): [10.1016/S0960-894X(00)80281-4]

3. McCluskey A, Sim AT, Sakoff JA..  (2002)  Serine-threonine protein phosphatase inhibitors: development of potential therapeutic strategies.,  45  (6): [PMID:11881984] [10.1021/jm010066k]

4. Fathi AR, Krautheim A, Kaap S, Eger K, Steinfelder HJ..  (2000)  Michael adducts of ascorbic acid as inhibitors of protein phosphatase 2A and inducers of apoptosis.,  10  (14): [PMID:10915062] [10.1016/s0960-894x(00)00294-8]

5. Gupta V, Ogawa AK, Du X, Houk KN, Armstrong RW..  (1997)  A model for binding of structurally diverse natural product inhibitors of protein phosphatases PP1 and PP2A.,  40  (20): [PMID:9379439] [10.1021/jm960873x]

6. McCluskey A, Keane MA, Walkom CC, Bowyer MC, Sim AT, Young DJ, Sakoff JA..  (2002)  The first two cantharidin analogues displaying PP1 selectivity.,  12  (3): [PMID:11814804] [10.1016/s0960-894x(01)00777-6]

7. Frydrychowski VA, Urbanek RA, Dounay AB, Forsyth CJ..  (2001)  Importance of the C28-C38 hydrophobic domain of okadaic acid for potent inhibition of protein serine-threonine phosphatases 1 and 2A.,  11  (5): [PMID:11266161] [10.1016/s0960-894x(01)00026-9]

8. Peng H, Xie W, Otterness DM, Cogswell JP, McConnell RT, Carter HL, Powis G, Abraham RT, Zalkow LH..  (2001)  Syntheses and biological activities of a novel group of steroidal derived inhibitors for human Cdc25A protein phosphatase.,  44  (5): [PMID:11262093] [10.1021/jm0004401]

9. Daranas AH, Fernández JJ, Morales EQ, Norte M, Gavín JA..  (2004)  Self-association of okadaic acid upon complexation with potassium ion.,  47  (1): [PMID:14695814] [10.1021/jm034189b]

10. Sakai R, Rinehart KL..  (1995)  A new polyether acid from a cold water marine sponge, a Phakellia species.,  58  (5): [PMID:7623052] [10.1021/np50119a021]

11. de Los Ríos C, Egea J, Marco-Contelles J, León R, Samadi A, Iriepa I, Moraleda I, Gálvez E, García AG, López MG, Villarroya M, Romero A..  (2010)  Synthesis, inhibitory activity of cholinesterases, and neuroprotective profile of novel 1,8-naphthyridine derivatives.,  53  (14): [PMID:20575555] [10.1021/jm901902w]

12. Konoki K, Saito K, Matsuura H, Sugiyama N, Cho Y, Yotsu-Yamashita M, Tachibana K..  (2010)  Binding of diarrheic shellfish poisoning toxins to okadaic acid binding proteins purified from the sponge Halichondria okadai.,  18  (21): [PMID:20863709] [10.1016/j.bmc.2010.08.043]

13. Liu L, Guo F, Crain S, Quilliam MA, Wang X, Rein KS..  (2012)  The structures of three metabolites of the algal hepatotoxin okadaic acid produced by oxidation with human cytochrome P450.,  20  (12): [PMID:22608922] [10.1016/j.bmc.2012.04.046]

14. Yang AR, Lee S, Yoo YD, Kim HS, Jeong EJ, Rho JR..  (2017)  Limaol: A Polyketide from the Benthic Marine Dinoflagellate Prorocentrum lima.,  80  (5): [PMID:28383915] [10.1021/acs.jnatprod.7b00127]

Source

Source(1):

• Scientific Literature