IDEA-AI4S/ChemO huggingface dataset:
IChO-2025_2
Points: 67
context: Rapamycin was isolated from the bacterium Streptomyces hygroscopicus in 1972. It acts as a molecular glue and inhibits the activity of the protein mTOR through binding to another protein. It has been used to treat various diseases. The stereochemical complexity of rapamycin makes its total synthesis challenging. The figure shows part of the first total synthesis by the Nicolaou group.
parsing_note: The molecular structure has been converted to SMILES format.
molecular_name: Rapamycin
smiles: C[C@@H]1CCC2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
IChO-2025_2.4
Type: Qualitative Identification
Points: 18
Question: context: The final steps of the enzymatic synthesis are shown below. The building blocks involved were determined by feeding the bacterium with three different ^{13}C -labelled starting materials which are incorporated into the monomers ^{13}C are circled as shown below: Circle the carbons in rapamycin that will be  ^{13}C -labelled when the bacterium is fed with each of the three starting materials a-c in turn, following the guidelines on the next page. Incorrect circles will be penalised but there is no negative scoring. Guidelines for circling carbon atoms: Do not include multiple carbon atoms in the same circle. Do not circle any bonds.
reaction_scheme: reactant_smiles: O=C(CC([C@H](C)CC[C@H](O)C[C@H](O)/C(C)=C/C=C/C=C/C(C)CC(C)C(C[C@H](O)/C(C)=C/C(C)C(C[C@H](O)[C@H](C)C[C@]1([H])CC[C@@H](O)[C@H](O)C1)=O)=O)=O)S[ACP]
conditions: O=C([C@H]1NCCCC1)O
product_formula: O[C@@]1(C(C(N2[C@]([H])(C(O[C@H]([C@H](C)C[C@@]3([H])C[C@@H](O)[C@H](O)CC3)CC([C@H](C)/C=C(C)/[C@@H](O)C4)=O)=O)CCCC2)=O)=O)O[C@@](C[C@H](O)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C4=O)([H])CC[C@H]1C
reactant_name: O[C@@]1(C(C(N2[C@]([H])(C(O[C@H]([C@H](C)C[C@@]3([H])C[C@@H](O)[C@H](O)CC3)CC([C@H](C)/C=C(C)/[C@@H](O)C4)=O)=O)CCCC2)=O)=O)O[C@@](C[C@H](O)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C4=O)([H])CC[C@H]1C
conditions: multiple steps
product_name: rapamycin
product_formula: C[C@@H]1CCC2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
^{13}C-labelled starting materials a: smiles: CCC(O[Na])=O
notes: From left to right, C-1 and C-2 are circled.
^{13}C-labelled starting materials b: smiles: CC(O[Na])=O
notes: From left to right, C-2 are circled.
^{13}C-labelled starting materials c: smiles: CC(O[Na])=O
notes: From left to right, C-1 are circled.
Answer: C-11, C-12, C-23, C-24, C-26, C-27, C-35, C-36, C-41, C-42, C-44, C-45, C-49, C-50
C-3, C-22, C-32, C-37, C-38, C-47, C-49
C-2, C-22, C-30, C-32, C-37, C-38, C-48