For this and the next few questions, you will consider the molecule lisinopril.

What is the SMILES string of lisinopril? (Hint: use PubChem to find its SMILES string)

Question

For this and the next few questions, you will consider the molecule lisinopril.

What is the SMILES string of lisinopril? (Hint: use PubChem to find its SMILES string)

BlackTom AI · Accepted Answer

The question asks for the SMILES string of lisinopril and notes to use PubChem to find it. In this instance, the provided data does not include multiple-choice options to evaluate, only a single answer string. I will nevertheless analyze the given SMILES and explain its components so you can judge its plausibility and how it encodes lisinopril’s structure.

First, consider what lisinopril is: a peptide-like ACE inhibitor built from an ingredient backbone that includes a dipeptide motif linked to a lysine residue, and with a terminal carboxylate group. It contains several stereocenters, amide bonds, carboxyl groups, and an aromatic phenyl moiety as part of the cap at the end of the molecule. A correct SMILES should reflect the amide linkages, the lysine side chain, the aromatic ring, and the terminal carboxylate groups, while preserving the stereochemistry at the chiral centers.

Option analysis (given single string):
- The string provided is: C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O. This SMILES uses stereochemical annotations [C@H] and [C@@H], which is appropriate because lisinopril possesses chiral centers. The ring notation C1...C1 indicates a cycloalkane ring fragment, which can correspond to part of lisinopril’s bicyclic or constrained ring structure seen in some ACE inhibitors; however, the canonical lisinopril structure is often depicted with a linear peptidomimetic chain rather than a simple cyclohexane ring. So, we should verify whether this particular ring closure accurately reflects lisinopril’s actual scaffold.
- The fragment N(C1)C(=O) suggests an N-substituted amide linked to the cyclo ring, which could correspond to a tertiary amide linkage in some representations. The presence of C(=O)O at the end indicates a terminal carboxylate group, consistent with lisinopril being a diacid derivative or having carboxylate termini in its salt forms.
- The [C@H](CCCCN) portion encodes a chiral carbon attached to a four-carbon chain ending in an amine, which matches the lysine-derived side chain often found in lisinopril. The subsequent N[C@@H](CCC2=CC=CC=C2) portion indicates an amide-linked portion bearing an anilide-like aryl group (phenyl ring), which aligns with the aromatic moiety that can appear in lisinopril’s side chain.
- The overall pattern C(=O)O at the end mirrors a carboxylate group; lisinopril typically has a carboxylate at the terminus (often shown as -COOH or -COO− in salt forms). This aligns with expected functional groups.

Potential concerns or ambiguities:
- Ring notation: The use of a cyclo ring (C1...C1) is not universally present in every lisinopril SMILES depiction. Some correct SMILES may use different ring closures or even a linear representation without a ring. If PubChem’s canonical SMILES uses a different ring configuration, this string might still be valid as a non-canonical or alternate representation, but it would not match the canonical SMILES if you compare directly.
- Stereochemistry: The presence of two chiral descriptors [C@H] and [C@@H] is appropriate for retaining stereochemical information. If PubChem’s canonical SMILES or InChI representation uses a different stereochemical specification, you would see identical stereochemical relationships but perhaps expressed with different notation or order.
- Aromatic moiety: The fragment CCC2=CC=CC=C2 represents a propenyl-phenyl-like group attached through a carbon chain to the amide. This is plausible for an ACE-inhibitor side chain, but some lisinopril representations might place the aromatic ring differently or use a substituted phenyl. The exact connectivity should be validated against a trusted source.

How you can verify:
- Cross-check with PubChem: search for lisinopril and inspect the canonical SMILES provided by PubChem. Compare ring closures, stereochemistry markers, and the order of substituents. PubChem’s canonical SMILES is designed to be a unique representation, which may differ from this string but should encode the same molecular structure.
- If you are learning SMILES conventions, try converting the given string into a 2D structure with a tool (e.g., RDKit or PubChem Sketcher) to visually inspect ring closures, stereochemistry, and functional groups. This helps confirm whether all features of lisinopril are present.

In summary, the single answer string contains realistic features expected in a lisinopril SMILES—stereochemical descriptors, amide and carboxylate functionalities, a lysine-like side chain, and a phenyl-containing fragment. However, without the multiple-choice options to compare against, we cannot determine whether this is the exact canonical SMILES listed by PubChem or another valid representation. The key aspects to verify with PubChem are the ring connectivity, the exact placement of stereochemistry, and the precise order of substituents around the amide bonds to ensure full structural fidelity.

2254 BIOSC 1544 SEC1000 Homework: Cheminformatics #2

For this and the next few questions, you will consider the molecule lisinopril. What is the SMILES string of lisinopril? (Hint: use PubChem to find its SMILES string)

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