methyl (2E)-3-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-yl]carbamoyl}prop-2-enoate hydrochloride

• ChemBase ID: 131089
• Molecular Formular: C25H31ClN2O6
• Molecular Mass: 490.97644
• Monoisotopic Mass: 490.1870644
• SMILES: COC(=O)/C=C/C(=O)N[C@@H]1CC[C@]2([C@@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3CC1CC1)O)O.Cl
• Canonical SMILES: COC(=O)/C=C/C(=O)N[C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)CC2CC2)ccc1O)O.Cl
• InChI: InChI=1S/C25H30N2O6.ClH/c1-32-20(30)7-6-19(29)26-16-8-9-25(31)18-12-15-4-5-17(28)22-21(15)24(25,23(16)33-22)10-11-27(18)13-14-2-3-14;/h4-7,14,16,18,23,28,31H,2-3,8-13H2,1H3,(H,26,29);1H/b7-6+;/t16-,18-,23+,24+,25-;/m1./s1
• InChIKey: BIPHUOBUKMPSQR-NQGXHZAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-3-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-yl]carbamoyl}prop-2-enoate hydrochloride
• IUPAC Traditional name: methyl (2E)-3-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-yl]carbamoyl}prop-2-enoate hydrochloride
• Synonyms: β-FNA hydrochloride; (E)-4-[[(5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]amino]-4-oxo-2-butenoic acid methyl ester hydrochloride; β-Funaltrexamine hydrochloride

Database IDs

• CAS Number: 72786-10-8
• MDL Number: MFCD10565941
• PubChem SID: 162225367; 24897921
• PubChem CID: 44522395

CALCULATED PROPERTIES

• Acid pKa: 10.292849
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.8903953
• LogD (pH = 7.4): -0.7450684
• Log P: 1.076977
• Molar Refractivity: 120.2326 cm^3
• Polarizability: 46.80448 Å^3
• Polar Surface Area: 108.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble7.5 mg/mL (aqueous solutions should be promptly used); methanol: soluble7.6 mg/mL (do not store in ethanolic solution; methanolic solutions may be stored for several weeks at 4 °C)
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - O003

Biochem/physiol Actions
Selective irreversible μ opioid receptor antagonist that is also a κ opioid receptor agonist.