(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,14,17-triol hydrate

• ChemBase ID: 153887
• Molecular Formular: C20H27NO5
• Molecular Mass: 361.43208
• Monoisotopic Mass: 361.18892297
• SMILES: c1cc(c2c3c1C[C@@H]1[C@]4([C@]3(CCN1CC1CC1)[C@@H](O2)[C@@H](CC4)O)O)O.O
• Canonical SMILES: O[C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O.O
• InChI: InChI=1S/C20H25NO4.H2O/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11;/h3-4,11,14-15,18,22-24H,1-2,5-10H2;1H2/t14-,15-,18+,19+,20-;/m1./s1
• InChIKey: VHGGWFVHXKTOPK-CDHBEYIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-triene-10,14,17-triol hydrate
• IUPAC Traditional name: (1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-triene-10,14,17-triol hydrate
• Synonyms: (5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-morphinan-3,6,14-triol hydrate; 6β-Naltrexol hydrate

Database IDs

• MDL Number: MFCD08277038
• PubChem SID: 162248026; 24724560
• PubChem CID: 16078992

CALCULATED PROPERTIES

• Acid pKa: 10.297444
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.1513104
• LogD (pH = 7.4): -0.9519057
• Log P: 0.8429298
• Molar Refractivity: 92.3989 cm^3
• Polarizability: 36.369213 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~12 mg/mL; H2O: insoluble
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C20H25NO4 · xH2O

DETAILS

Sigma Aldrich - N9412

Biochem/physiol Actions
Neutral antagonist of the μ-opioid receptor. A reduction of withdrawal effects associated with neutral μ-opioid receptor antagonists may offer advantages in treating opioid overdose and addiction.