(1S,2S,13R,21R)-22-(cyclopropylmethyl)-9-isothiocyanato-14-oxa-11,22-diazaheptacyclo[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 hydrochloride

• ChemBase ID: 133007
• Molecular Formular: C27H26ClN3O3S
• Molecular Mass: 508.03164
• Monoisotopic Mass: 507.13834039
• SMILES: c1cc2c3c([nH]c2c(c1)N=C=S)[C@H]1[C@@]24CCN([C@H]([C@@]2(C3)O)Cc2c4c(c(cc2)O)O1)CC1CC1.Cl
• Canonical SMILES: S=C=Nc1cccc2c1[nH]c1c2C[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)CC2CC2)ccc1O)O.Cl
• InChI: InChI=1S/C27H25N3O3S.ClH/c31-19-7-6-15-10-20-27(32)11-17-16-2-1-3-18(28-13-34)22(16)29-23(17)25-26(27,21(15)24(19)33-25)8-9-30(20)12-14-4-5-14;/h1-3,6-7,14,20,25,29,31-32H,4-5,8-12H2;1H/t20-,25+,26+,27-;/m1./s1
• InChIKey: SYDXFYIGIIAPLB-OKRPGNDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,13R,21R)-22-(cyclopropylmethyl)-9-isothiocyanato-14-oxa-11,22-diazaheptacyclo[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 hydrochloride
• IUPAC Traditional name: (1S,2S,13R,21R)-22-(cyclopropylmethyl)-9-isothiocyanato-14-oxa-11,22-diazaheptacyclo[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 hydrochloride
• Synonyms: NTII; Naltrindole isothiocyanate hydrochloride

Database IDs

• CAS Number: 126876-64-0
• PubChem SID: 162227284
• PubChem CID: 71308617

CALCULATED PROPERTIES

• Acid pKa: 10.12893
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2978246
• LogD (pH = 7.4): 3.0158577
• Log P: 4.0909734
• Molar Refractivity: 134.8445 cm^3
• Polarizability: 52.469334 Å^3
• Polar Surface Area: 81.08 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble3.3 mg/mL; DMSO: soluble; ethanol: slightly soluble; H2O: insoluble
• Apperance: off-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 - N157

Biochem/physiol Actions
Selective irreversible δ2 opioid receptor antagonist.