Isotretinoin

C₂₀H₂₈O₂CAS 4759-48-2300.44 g/mol

Open in Covalent MOL file

Alkene Carboxylic acid

Properties

Molecular formula: C₂₀H₂₈O₂
Molar mass: 300.44 g/mol
Exact mass: 300.2089 Da
Melting point: 174–175 °C
pKa: 5.15
Water solubility: < 1 g/L (22.2 °C)
logP: 5.60Crippen estimate
Polar surface area: 37.3 Å²
H-bond donors / acceptors: 1 / 1
Rotatable bonds: 5
Double bonds: E, E, EE/Z, in SMILES order

Hazards

Danger

H315 Causes skin irritation30.7% of notifiers
H319 Causes serious eye irritation31.4% of notifiers
H335 May cause respiratory irritation30.1% of notifiers
H360 May damage fertility or the unborn child100% of notifiers
H400 Very toxic to aquatic life71.2% of notifiers
H410 Very toxic to aquatic life with long lasting effects71.9% of notifiers

Aggregated from 153 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P203, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501

Identifiers

CAS number

4759-48-2

SMILES

CC1=C(/C=C/C(C)=C/C=C/C(C)=CC(=O)O)C(C)(C)CCC1

InChIKey

SHGAZHPCJJPHSC-XFYACQKRSA-N

InChI

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

20 names · show all

Retinoic acid, 13-cis-
13-cis-Retinoic acid
Neovitamin A acid
13-cis-Vitamin A acid
Ro 4-3780
13-cis-β-Retinoic acid
(13Z)-Retinoic acid
Accutane
Roaccutane
AGN 190013
Roaccutan
Accure
13-RA
Isotrex
IsotrexGel
cis-Retinoic acid
Absorica
Amnesteem
Claravis
Roacutan

Work with Isotretinoin

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Retinoic acid302-79-4Stereoisomer 9-cis-Retinoic acid5300-03-8Stereoisomer

Similar compounds

Beta-carotene7235-40-773 % similar Retinal116-31-469 % similar Vitamin A11103-57-466 % similar Retinol68-26-866 % similar Retinyl retinoate15498-86-965 % similar Hydroxypinacolone retinoate893412-73-263 % similar Retinyl acetate127-47-962 % similar Fenretinide65646-68-662 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Same formula

17Beta-Hydroxy-17-methylandrosta-4,9(11)-dien-3-one1039-17-4 5,8,11-Eicosatriynoic acid13488-22-7 Dehydroabietic acid1740-19-8 13-Ethyl-3-methoxygona-2,5(10)-dien-17-one2322-77-2 Methandrostenolone72-63-9

Elsewhere

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