(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-15-(phenylmethylidene)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-one but-2-enedioic acid hydrate

• ChemBase ID: 154501
• Molecular Formular: C31H33NO9
• Molecular Mass: 563.59502
• Monoisotopic Mass: 563.21553164
• SMILES: c1ccc(cc1)/C=C/1\C[C@]2([C@H]3Cc4ccc(c5c4[C@@]2(CCN3CC2CC2)[C@H](C1=O)O5)O)O.C(=C\C(=O)O)/C(=O)O.O
• Canonical SMILES: O=C1/C(=C/c2ccccc2)/C[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O.OC(=O)/C=C/C(=O)O.O
• InChI: InChI=1S/C27H27NO4.C4H4O4.H2O/c29-20-9-8-18-13-21-27(31)14-19(12-16-4-2-1-3-5-16)23(30)25-26(27,22(18)24(20)32-25)10-11-28(21)15-17-6-7-17;5-3(6)1-2-4(7)8;/h1-5,8-9,12,17,21,25,29,31H,6-7,10-11,13-15H2;1-2H,(H,5,6)(H,7,8);1H2/t21-,25+,26+,27-;;/m1../s1
• InChIKey: AGUNLJBLOJAUKM-VIBIRNFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-15-(phenylmethylidene)-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-one but-2-enedioic acid hydrate
• IUPAC Traditional name: (1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-15-(phenylmethylidene)-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-one butenedioic acid hydrate
• Synonyms: 7(E)-Benzylidenenaltrexone maleate salt hydrate; BNTX-7 maleate salt hydrate; Morphinan-6-one,17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-7-(phenylmethylene)-,(5a,7E)- maleate salt hydrate; BNTX maleate salt hydrate

Database IDs

• MDL Number: MFCD12912399
• PubChem SID: 162248640
• PubChem CID: 71311879

CALCULATED PROPERTIES

• Acid pKa: 10.108033
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.54487807
• LogD (pH = 7.4): 2.156253
• Log P: 3.4112062
• Molar Refractivity: 121.6479 cm^3
• Polarizability: 47.15001 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: powder, yellow

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36-50/53
• Safety Statements: 26-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H400
• GHS Precautionary statements: P273-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C31H31NO8 · xH2O

DETAILS

Sigma Aldrich - B8312

Biochem/physiol Actions
BNTX is a selective nonpeptide δ1 opioid receptor antagonist. It antagonizes the effect of D-Pen2,5-enkephalin (a δ1 agonist 4-6 fold, but did not affect the activity of δ2 or μ agonists.<<<107>>> BNTX is used to discriminate among opioid receptor subtypes in effects such as alcohol and drug dependence. It binds 100× more tightly to δ1 than to δ2 receptors. In the tail-flick assay, antinocieceptive ED50 = 646.4 pmol/mouse.