Efavirenz

C14H9ClF3NO2, 315.678 g/mol. Its structure, the values that were measured, the values that were calculated, and where each one came from.

verified recordOrganic — aromatic ester3 measured properties

Drawn from the SMILES. It shows how the atoms are connected — not a photograph of a molecule, and not its shape in space.

Identifiers

Molecular formula: C₁₄H₉ClF₃NO₂
Molecular weight: 315.678 g/mol
Exact mass: 315.027391 g/mol
IUPAC name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
SMILES: O=C1Nc2ccc(Cl)cc2C(C#CC2CC2)(C(F)(F)F)O1
Isomeric SMILES: O=C1Nc2ccc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1
InChI: InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1
InChIKey: XPOQHMRABVBWPR-ZDUSSCGKSA-N

Open in ReactionLens Use in reaction prediction

Both are open without an account.

Measured properties

Values somebody obtained from a sample and published. Where two sources report the same property they are both shown, in the units each used — a disagreement between them is information, and averaging it away would be inventing a number neither one gave.

Melting Point: 139-141 °Cmeasured · DrugBank; 139-141 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: Practically insoluble in water (less than 10 mg/L)measured · Hazardous Substances Data Bank (HSDB); 8.55e-03 g/Lmeasured · Human Metabolome Database (HMDB)
LogP: 4.6measured · DrugBank; 4.6measured · Human Metabolome Database (HMDB)

Calculated properties

Derived from the structure rather than from a sample. These are reproducible and they are not measurements: a calculated partition coefficient and a measured one can differ by a long way, and where both exist they are listed apart on purpose.

Molecular weight: 315.67 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 315.0273907 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 4calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 38.3 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 519calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 5calculated · reference compound database
logP: 4.0731calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 38.33 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: 2calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 69.7887 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.3571calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.7328calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon14 atoms · 53.3% by mass
F Fluorine3 atoms · 18.1% by mass
Cl Chlorine1 atom · 11.2% by mass
O Oxygen2 atoms · 10.1% by mass
N Nitrogen1 atom · 4.4% by mass
H Hydrogen9 atoms · 2.9% 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: 21
Total atoms, hydrogen included: 30
Rings: 3
Aromatic rings: 1
Stereocentres: 1
Formal charge: 0

Functional groups

Ester
A carbonyl bonded to an oxygen that links to another carbon.
Amide
A carbonyl bonded directly to nitrogen.
Ether
An oxygen bridging two carbons.
Halide (C–X)
A halogen atom attached to carbon.
Alkyne
A carbon–carbon triple bond.
Aromatic ring
A flat six-membered ring with delocalised electrons.

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 Efavirenz yet.

Other names for it

The systematic name on this record is (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one.

The sources also call it Sustiva, Stocrin, (-)-Efavirenz, Viraday, Efavirenz teva, Efavirenzum.

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.

(3-Chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acid benzyl ester

C14H9ClF3NO2

Where these values came from

reference compound database64139
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

The identifiers are what the source record holds, copied rather than recomputed. Measured values are reported as their source gave them, units and all; calculated values are marked as calculated and are not measurements. Where a field is absent the page says so, because a blank cell reads as a zero and a guessed value reads as a fact.

Nothing here is a hazard assessment, a purity statement or advice about handling a sample. A flash point quoted from a safety database is a number somebody published, not a judgement by us about whether this molecule is safe for what you intend.