Payload Information

General Information of This Payload
Payload ID
PAY0KBXUQ
Name
Spliceostatin A
Synonyms
Spliceostatin A; 391611-36-2; [(Z,2S)-4-[[(2R,3R,5S,6S)-6-[(2E,4E)-5-[(3R,4R,5R,7S)-4-hydroxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methylpenta-2,4-dienyl]-2,5-dimethyloxan-3-yl]carbamoyl]but-3-en-2-yl] acetate; CHEMBL1221942; SCHEMBL18134895; EX-A6219; BP-28004; HY-16466; CS-0006350; Q59780090; (2Z,4S)-N-[(2R,3R,5S,6S)-2,5-Dimethyl-6-[(2E)-3-methyl-5-[(3R,4R,5R,7S)-4-hydroxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]octane-5-yl]-2,4-pentadienyl]tetrahydro-2H-pyran-3-yl]-4-acetoxy-2-penteneamide; [(Z,2S)-5-[[(2R,3R,5S,6S)-6-[(2E,4E)-5-[(3R,4R,5R,7S)-4-hydroxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methylpenta-2,4-dienyl]-2,5-dimethyloxan-3-yl]amino]-5-oxopent-3-en-2-yl] acetate
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Target(s) Splicing factor 3B subunit 1 (SF3B1)
 Target Info 
Structure
Formula
C28H43NO8
Isosmiles
C[C@H]1C[C@H]([C@H](O[C@H]1C/C=C(\C)/C=C/[C@@H]2[C@H]([C@@]3(C[C@@](O2)(C)OC)CO3)O)C)NC(=O)/C=C\[C@H](C)OC(=O)C
PubChem CID
10673568
InChI
InChI=1S/C28H43NO8/c1-17(9-12-24-26(32)28(16-34-28)15-27(6,33-7)37-24)8-11-23-18(2)14-22(20(4)36-23)29-25(31)13-10-19(3)35-21(5)30/h8-10,12-13,18-20,22-24,26,32H,11,14-16H2,1-7H3,(H,29,31)/b12-9+,13-10-,17-8+/t18-,19-,20+,22+,23-,24+,26+,27-,28+/m0/s1
InChIKey
XKSGIJNRMWHQIQ-CGPJBNNXSA-N
IUPAC Name
[(Z,2S)-5-[[(2R,3R,5S,6S)-6-[(2E,4E)-5-[(3R,4R,5R,7S)-4-hydroxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methylpenta-2,4-dienyl]-2,5-dimethyloxan-3-yl]amino]-5-oxopent-3-en-2-yl] acetate
Pharmaceutical Properties
Molecule Weight
521.6
Polar area
116
Complexity
916
xlogp Value
2.6
Heavy Count
37
Rot Bonds
10
Hbond acc
8
Hbond Donor
2
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Inhibitory Concentration (IC50) 0.6 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[1]
Half Maximal Inhibitory Concentration (IC50) 0.6 nM
22RV1 cells
Prostate carcinoma
CVCL_1045 
[2]
Half Maximal Inhibitory Concentration (IC50) 10 nM
HeLa cells
Endocervical adenocarcinoma
CVCL_0030 
[3]
Each Antibody-drug Conjugate Related to This Payload
References
Ref 1 Methoxylation of 3',4'-aromatic side chains improves P-glycoprotein inhibitory and multidrug resistance reversal activities of 7,8-pyranocoumarin against cancer cells. Bioorg Med Chem. 2008 Apr 1;16(7):3694-703. doi: 10.1016/j.bmc.2008.02.029. Epub 2008 Feb 13.
Ref 2 Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment. ACS Med Chem Lett. 2020 May 1;11(6):1310-1315. doi: 10.1021/acsmedchemlett.0c00153. eCollection 2020 Jun 11.
Ref 3 Spliceostatins and Derivatives: Chemical Syntheses and Biological Properties of Potent Splicing Inhibitors. J Nat Prod. 2021 May 28;84(5):1681-1706. doi: 10.1021/acs.jnatprod.1c00100. Epub 2021 May 11.

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