(1S,2S,13R,21R)-22-(cyclopropylmethyl)-11,14-dioxa-22-azaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol methanesulfonic acid hydrate

• ChemBase ID: 155544
• Molecular Formular: C27H31NO8S
• Molecular Mass: 529.60194
• Monoisotopic Mass: 529.17703796
• SMILES: CS(=O)(=O)O.c1ccc2c(c1)c1c(o2)[C@H]2[C@@]34CCN([C@@H]([C@@]3(C1)O)Cc1c4c(c(cc1)O)O2)CC1CC1.O
• Canonical SMILES: CS(=O)(=O)O.Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)Cc2c1oc1c2cccc1)CC1CC1.O
• InChI: InChI=1S/C26H25NO4.CH4O3S.H2O/c28-18-8-7-15-11-20-26(29)12-17-16-3-1-2-4-19(16)30-22(17)24-25(26,21(15)23(18)31-24)9-10-27(20)13-14-5-6-14;1-5(2,3)4;/h1-4,7-8,14,20,24,28-29H,5-6,9-13H2;1H3,(H,2,3,4);1H2/t20-,24+,25+,26-;;/m1../s1
• InChIKey: VAGWKZSGWSRENH-HIAJFTJMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,13R,21R)-22-(cyclopropylmethyl)-11,14-dioxa-22-azaheptacyclo[13.9.1.0^1,^1^3.0^2,^2^1.0^4,^1^2.0^5,^1^0.0^1^9,^2^5]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol methanesulfonic acid hydrate
• IUPAC Traditional name: methanesulfonic acid naltriben hydrate
• Synonyms: NTB hydrate; Naltriben methanesulfonate hydrate

Database IDs

• MDL Number: MFCD11046015
• PubChem SID: 162249682; 24278045
• PubChem CID: 16219722

CALCULATED PROPERTIES

• Acid pKa: 10.112982
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5937983
• LogD (pH = 7.4): 2.3634079
• Log P: 3.2100027
• Molar Refractivity: 115.5362 cm^3
• Polarizability: 45.93531 Å^3
• Polar Surface Area: 66.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble14 mg/mL at ~60 °C
• Apperance: off-white solid

Safety Information

• RTECS: PB9175000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C26H25NO4 · CH4O3S · xH2O

DETAILS

Sigma Aldrich - N156

Biochem/physiol Actions
Naltriben methanesulfonate is a highly selective δ2 opioid receptor antagonist. The relative ability of the delta antagonists benzylidenenaltrexone and naltriben to inhibit DPDPE-stimulated [35S]GTPgammaS binding suggests that the opioid receptor is of the delta-2 subtype. Ligand binding assays demonstrates biphasic binding of the antagonist to the single receptor type. [35S]GTPgammaS binding is also stimulated by [D-Ser2,Leu5,Thr6]enkepha