Synonyms: (-)-calyculin A | hemicalyculin A
Compound class:
Natural product
Comment: Calyculin A is a natural product that has been isolated from the marine sponges Lamellomorpha strongylata and Discodermia calyx.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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19
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Hydrogen bond donors
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8
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Rotatable bonds
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27
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Topological polar surface area
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292.36
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Molecular weight
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1009.17
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XLogP
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1.19
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No. Lipinski's rules broken
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4
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Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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SMILES / InChI / InChIKey
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Canonical SMILES
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C/C(=C/C#N)/C=C/C=C(\C)/C(=C/[C@@H](C)[C@H]([C@@H](C)[C@H](C[C@@H]([C@@H]1[C@@H](C(C)(C)[C@@]2(C[C@H]([C@H](C)[C@H](C/C=C/C3=COC(=N3)[C@@H](C)CCNC(=O)[C@H]([C@H]([C@H](COC)N(C)C)O)O)O2)O)O1)OP(=O)(O)O)OC)O)O)/C
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Isomeric SMILES
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C[C@H]1[C@@H](C[C@@]2(C([C@H]([C@H](O2)[C@H](C[C@@H]([C@H](C)[C@@H]([C@H](C)/C=C(\C)/C(=C/C=C/C(=C\C#N)/C)/C)O)O)OC)OP(=O)(O)O)(C)C)O[C@H]1C/C=C/C3=COC(=N3)[C@@H](C)CCNC(=O)[C@H]([C@H]([C@H](COC)N(C)C)O)O)O
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InChI
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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
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InChI Key
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FKAWLXNLHHIHLA-YCBIHMBMSA-N
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Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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