(RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester

An aromatic ester, C22H17ClFN3O5S, 489.912 g/mol.

verified recordOrganic — aromatic ester

Identifiers

Molecular formula: C₂₂H₁₇ClFN₃O₅S
Molecular weight: 489.912 g/mol
Exact mass: 489.056148 g/mol
IUPAC name: methyl 5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,2,4-oxadiazole-3-carboxylate
SMILES: COC(=O)c1noc(C(F)(C2Cc3[nH]c4ccc(Cl)cc4c3C2)S(=O)(=O)c2ccccc2)n1
InChI: InChI=1S/C22H17ClFN3O5S/c1-31-20(28)19-26-21(32-27-19)22(24,33(29,30)14-5-3-2-4-6-14)12-9-15-16-11-13(23)7-8-17(16)25-18(15)10-12/h2-8,11-12,25H,9-10H2,1H3
InChIKey: ZEJSYWOLUBDLES-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 489.9 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 489.0561477 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 4.4calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 124 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 853calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 8calculated · reference compound database
logP: 4.0021calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 115.15 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 1calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 7calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 5calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 116.258 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.2273calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.4211calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon22 atoms · 53.9% by mass
O Oxygen5 atoms · 16.3% by mass
N Nitrogen3 atoms · 8.6% by mass
Cl Chlorine1 atom · 7.2% by mass
S Sulfur1 atom · 6.5% by mass
F Fluorine1 atom · 3.9% by mass
H Hydrogen17 atoms · 3.5% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 33
Total atoms, hydrogen included: 50
Rings: 5
Aromatic rings: 4
Stereocentres: 2
Formal charge: 0

Functional groups

Ester
A carbonyl bonded to an oxygen that links to another carbon.
Ether
An oxygen bridging two carbons.
Halide (C–X)
A halogen atom attached to carbon.
Aromatic ring
A flat six-membered ring with delocalised electrons.
Aromatic ring (five-membered)
A flat five-membered ring with delocalised electrons, such as furan, thiophene or pyrrole.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester yet.

Other names for it

The systematic name on this record is methyl 5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,2,4-oxadiazole-3-carboxylate.

The sources also call it SCHEMBL1377593, ZEJSYWOLUBDLES-UHFFFAOYSA-N.

Structurally related

Molecules sharing this formula, or whose fingerprint is at least 40% similar to this one. Similarity is Tanimoto on Morgan fingerprints over this library only — it is a measure of structural overlap, not of how alike they behave.

(RS,SR)-N-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-acetamide

C23H20ClFN4O4S

(RS,SR)-C-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-yl}-methylamine

C21H18ClFN4O3S

(RS,SR)-2-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-isoindole-1,3-dione

C29H20ClFN4O5S

(RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester

C22H22ClNO4S

(RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole

C22H24ClNO3S

(RS,SR)-2-benzenesulfonyl-2-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester

C22H22BrNO4S

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.