Phosphoric acid mono-{3,10-dihydroxy-1-[1-hydroxy-1-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester

ID: ALA3991199

Chembl Id: CHEMBL3991199

PubChem CID: 6436285

Max Phase: Unknown

Molecular Formula: C19H27O9P

Molecular Weight: 430.39

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Phosphotrienin | CL 1565A | CL-1565A | NSC-339638 | SCHEMBL62527|CHEMBL3991199|[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]trideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate|NS00011778

Synonyms from Alternative Forms(2): Fostriecin sodium | CI-920

Canonical SMILES:  C[C@@](O)(/C=C/[C@@H]1CC=CC(=O)O1)[C@@H](C[C@@H](O)/C=C\C=C/C=C/CO)OP(=O)(O)O

Standard InChI:  InChI=1S/C19H27O9P/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26)/b3-2-,6-4+,8-5-,12-11+/t15-,16-,17+,19+/m0/s1

Standard InChI Key:  ZMQRJWIYMXZORG-GZIFKOAOSA-N

Alternative Forms

  1. Alternative Forms:

  2. Parent:

    ALA3991199

    FOSTRIECIN

Associated Targets(Human)

HCT-8 (3484 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Serine-threonine protein phosphatase 2A regulatory subunit (96 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Top2 DNA topoisomerase II (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 430.39Molecular Weight (Monoisotopic): 430.1393AlogP: 1.06#Rotatable Bonds: 11
Polar Surface Area: 153.75Molecular Species: ACIDHBA: 7HBD: 5
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 1.53CX Basic pKa: CX LogP: 0.63CX LogD: -2.63
Aromatic Rings: Heavy Atoms: 29QED Weighted: 0.14Np Likeness Score: 2.44

References

1. McCluskey A, Sim AT, Sakoff JA..  (2002)  Serine-threonine protein phosphatase inhibitors: development of potential therapeutic strategies.,  45  (6): [PMID:11881984] [10.1021/jm010066k]
2. McCluskey A, Bowyer MC, Collins E, Sim ATR, Sakoff JA, Baldwin ML..  (2000)  Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity.,  10  (15): [PMID:10937725] [10.1016/s0960-894x(00)00323-1]
3. Takeuchi T, Takahashi N, Ishi K, Kusayanagi T, Kuramochi K, Sugawara F..  (2009)  Antitumor antibiotic fostriecin covalently binds to cysteine-269 residue of protein phosphatase 2A catalytic subunit in mammalian cells.,  17  (23): [PMID:19857968] [10.1016/j.bmc.2009.09.050]
4. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]
5. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]
6. Takeuchi T, Imai T, Ishi K, Saitoh T, Kuramochi K, Sugawara F.  (2011)  The anti-tumor antibiotic PD 113,271 binds to microtubule-associated protein 1B (MAP1B),  (12): [10.1039/C1MD00080B]

Source