(1S,2R,6S)-3-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol

• ChemBase ID: 1333
• Molecular Formular: C26H35NO4
• Molecular Mass: 425.5604
• Monoisotopic Mass: 425.25660861
• SMILES: O1C2[C@]34[C@@]5([C@H](N(CC3)CC3CC3)Cc3c4c1c(O)cc3)CC(C2(OC)CC5)C(O)(C)C
• Canonical SMILES: COC12CC[C@]3(CC1C(O)(C)C)[C@@]14C2Oc2c4c(C[C@H]3N(CC1)CC1CC1)ccc2O
• InChI: InChI=1S/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18?,19-,22?,24-,25+,26?/m1/s1
• InChIKey: OIJXLIIMXHRJJH-USQHPYHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S)-3-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol
• IUPAC Traditional name: diprenorphine
• Synonyms: Diprenorphine

Database IDs

• CAS Number: 14357-78-9
• PubChem SID: 46506559; 160964793
• PubChem CID: 26644

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.41544
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.6781455
• LogD (pH = 7.4): 0.34461454
• Log P: 2.2844017
• Molar Refractivity: 118.3686 cm^3
• Polarizability: 46.749737 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.52
• LOG S: -3.61
• Solubility (Water): 1.04e-01 g/l

DETAILS

DrugBank - DB01548

• Drug Groups: illicit; experimental
• Description: A narcotic antagonist similar in action to naloxone. It is used to remobilize animals after etorphine neuroleptanalgesia and is considered a specific antagonist to etorphine. [PubChem]
• Indication: Diprenorphine is used to reverse the effects of the super-potent opioid analgesics such as etorphine and carfentanil that are used for tranquilizing large animals in veterinary medicine. Not used in humans.
• External Links: Wikipedia