General Information of the Compound
Compound ID
CP0069870
Compound Name
17-cyclobutylmethyl-4,5alpha-epoxymorphinan-3,6alpha,14-triol
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Synonyms
(5alpha,6alpha)-17-(cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol
17-cyclobutylmethyl-4,5alpha-epoxymorphinan-3,6alpha,14-triol
Intapan
Intapan (TN)
Nalbufina
Nalbuphine
Nalbuphine (INN)
Nalbuphinum
Nubain (TN)
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Structure
Formula
C21H27NO4
Molecular Weight
357.45
Canonical SMILES
O[C@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5O[C@@H]1[C@]2(CCN3CC1CCC1)c45
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InChI
InChI=1S/C21H27NO4/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12/h4-5,12,15-16,19,23-25H,1-3,6-11H2/t15-,16+,19-,20-,21+/m0/s1
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InChIKey
NETZHAKZCGBWSS-CEDHKZHLSA-N
CAS
20594-83-6
Physicochemical Property
logP
1.7073
Rotatable Bonds
2
Heavy Atom Count
26
Polar Areas
73.16
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Complexity
26

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 5311304
SID: 14828107
ChEMBL ID
CHEMBL895
DrugBank ID
DB00844
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01200, Delta-type opioid receptor
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO
 Cell Line Info 
Cricetulus griseus (Chinese hamster)  2
1
Ki = 240 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
Ki = 580 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 353 nM
2 Ki = 318.85 nM
Protein ID: PT00983, Kappa-type opioid receptor
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO
 Cell Line Info 
Cricetulus griseus (Chinese hamster)  5
1
EC50 = 27 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 56 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
EC50 = 65 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
Ki = 2.2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
5
Ki = 3 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000043 U2OS
 Cell Line Info 
Homo sapiens (Human)  1
1
EC50 = 250 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 83 nM
2 Ki = 29.95 nM
Protein ID: PT01515, Mu-type opioid receptor
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO
 Cell Line Info 
Cricetulus griseus (Chinese hamster)  6
1
EC50 = 14 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 46 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
IC50 = 96 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
IC50 = 110 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
5
Ki = 0.89 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
6
Ki = 1.6 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 1 nM
2 Ki = 14.31 nM
Clinical Information about the Compound
Drug 1 ( Nalbuphine )
Drug Name Nalbuphine
Company Endo Pharmaceuticals
Indication
Pain
Phase 3
Prurigo nodularis
Phase 2/3
Uremic pruritus
Phase 2/3
Target(s)
Opioid receptor kappa (OPRK1)
 Target Info 
Modulator