Molecule

Calyculin A

AlkaPlorer ID: AK005468

Synonym: None

IUPAC Name: [(2R,3R,5R,7R,8S,9S)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl]-9-[(E)-3-[2-[(2S)-4-[[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanoyl]amino]butan-2-yl]-1,3-oxazol-4-yl]prop-2-enyl]-7-hydroxy-4,4,8-trimethyl-1,10-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate

Structure

SMILES: COC[C@@H]([C@H](O)[C@H](O)C(=O)NCC[C@H](C)C1=NC(/C=C/C[C@@H]2O[C@]3(C[C@@H](O)[C@@H]2C)O[C@H]([C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C(C)/C(C)=C/C=C/C(C)=C\C#N)OC)[C@H](OP(=O)(O)O)C3(C)C)=CO1)N(C)C

InChI: InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1

InChIKey: FKAWLXNLHHIHLA-YCBIHMBMSA-N

Reference

Calyculins E, F, G, and H, additional inhibitors of protein phosphatases 1 and 2a, from the marine sponge discodermia calyx

PubChem CID: 5311365

CAS: 101932-71-2

LOTUS: LTS0252021

SuperNatural Ⅲ: SN0087832-22

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NPAtlas: NPA024784

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
bacterium	None	None	None	None	None	None	Bacteria

Properties Information

Molecule Weight: 1009.185

TPSA？: 286.98999999999995

MolLogP？: 4.688980000000007

Number of H-Donors: 8

Number of H-Acceptors: 16

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Gallus gallus	Serine-threonine protein phosphatase 2A regulatory subunit	IC50	0.2	nM	10.1021/jm010066k
Gallus gallus	Serine-threonine protein phosphatase 2A regulatory subunit	IC50	2.0	nM	10.1016/s0960-894x(01)00777-6
Gallus gallus	Serine-threonine protein phosphatase 2A regulatory subunit	IC50	7.3	nM	10.1021/jm960873x
Homo sapiens	DNA-(apurinic or apyrimidinic site) lyase	Potency	2238.7	nM	None
Homo sapiens	Huntingtin	Potency	1000.0	nM	None
Homo sapiens	Huntingtin	Potency	1122.0	nM	None
Homo sapiens	Protein-tyrosine phosphatase 1B	IC50	0.3	nM	10.1016/S0960-894X(00)80281-4
Homo sapiens	Protein-tyrosine phosphatase 1B	IC50	0.5	nM	10.1016/s0960-894x(01)00777-6
Homo sapiens	Protein-tyrosine phosphatase 1B	IC50	1.2	nM	10.1021/jm960873x
Homo sapiens	Serine/threonine protein phosphatase 2A, 56 kDa regulatory subunit, alpha isoform	IC50	0.13	nM	10.1016/S0960-894X(00)80281-4
Homo sapiens	Serine/threonine protein phosphatase 2A, catalytic subunit, alpha isoform	IC50	0.25	nM	10.1021/acs.jmedchem.1c00631
Homo sapiens	Serine/threonine-protein phosphatase 5	IC50	3.0	nM	10.1021/acs.jmedchem.1c00631
Homo sapiens	Serine/threonine-protein phosphatase 6 catalytic subunit	IC50	10.0	nM	10.1021/acs.jmedchem.1c00631
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	0.14	nM	10.1021/jm010066k
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	0.4	nM	10.1021/jm010066k
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	0.45	nM	10.1021/jm010066k
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	2.2	nM	10.1021/jm010066k
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	48.0	nM	10.1021/jm010066k
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	58.0	nM	10.1021/jm010066k
Homo sapiens	Serine/threonine protein phosphatase PP1-gamma catalytic subunit	IC50	500.0	nM	10.1021/jm010066k
Mus musculus	Mus musculus	ED50	2.8	nM	10.1016/S0960-894X(00)80281-4
Mus musculus	Nuclear receptor ROR-gamma	Potency	0.01413	nM	None
Mus musculus	Nuclear receptor ROR-gamma	Potency	1.4	nM	None
Rattus norvegicus	Inositol monophosphatase 1	Potency	39.8	nM	None
Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	nan	None	10.1038/nchembio.100
Spodoptera littoralis	Spodoptera littoralis	LD50	1.0	ug	10.1021/np020049d
None	Unchecked	IC50	0.2	nM	10.1021/acs.jmedchem.1c00631
None	Unchecked	IC50	0.3	nM	10.1021/jm010066k
None	Unchecked	IC50	0.9	nM	10.1021/np50078a001
None	Unchecked	IC50	1.5	nM	10.1021/acs.jmedchem.1c00631
None	Unchecked	IC50	3.0	nM	10.1021/jm010066k
None	Unchecked	IC50	1000.0	nM	10.1021/acs.jmedchem.1c00631
None	Unchecked	IC50	10000000.0	nM	10.1021/jm010066k
None	Unchecked	IC50	nan	None	10.1021/jm010066k
None	Unchecked	Potency	0.8	nM	None
None	Unchecked	Potency	18.4	nM	None
None	Unchecked	Potency	41.1	nM	None