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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014982

Secondary Accession Numbers

HMDB14982

Metabolite Identification

Common Name

Nalbuphine

Description

Nalbuphine is only found in individuals that have used or taken this drug. It is a narcotic used as a pain medication. It appears to be an agonist at kappa opioid receptors and an antagonist or partial agonist at mu opioid receptors. [PubChem]The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Nalbuphine is thought primarily to be a kappa agonist. It is also a partial mu antagonist analgesic, with some binding to the delta receptor and minimal agonist activity at the sigma receptor.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 04191212152D          

 26 31  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4435    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8374   -1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8374   -2.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -2.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 11  1  0  0  0  0
 15  1  1  0  0  0  0
  2 16  1  0  0  0  0
  1  6  2  0  0  0  0
  2  1  1  0  0  0  0
  5  2  2  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
 10 13  1  0  0  0  0
 16 13  1  0  0  0  0
 16  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  1  0  0  0
 12 18  1  0  0  0  0
 13 14  1  1  0  0  0
 11 15  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
  8 19  1  6  0  0  0
  5 20  1  0  0  0  0
  7 20  1  6  0  0  0
  4 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 24  1  0  0  0  0
M  END

HMDB0014982
     RDKit          3D
Nalbuphine
 53 58  0  0  0  0  0  0  0  0999 V2000
    5.2912   -1.4565    1.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0482   -1.5834    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118   -2.7829    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654   -2.8930   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5274   -1.7798   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -0.6437    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -0.4893    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658    0.8521    1.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    1.5918    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9514    2.1700   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0704    1.3728   -0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469    2.2066   -1.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137    0.9048   -1.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.7225   -0.7888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3326    1.8622   -0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -0.4670   -0.9174 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1778   -1.8083   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -0.2609   -0.0003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    0.1865   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459    0.4053    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -0.8247    1.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5074   -0.9581    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2213    0.3888   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.3832    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769    0.5881    1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1825    0.6025    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8980   -2.2514    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786   -3.6210    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0204   -3.8200   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615    2.4121    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.1885   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6940    1.3035    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    3.0715   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.3611   -2.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330    0.1018   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    1.0184   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4298    2.2767   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887   -0.4422   -1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -2.4518   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079   -2.3726   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -0.6421   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081    1.1216   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    1.3293    0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5173   -0.5754    2.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -1.6662    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -1.8173   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575   -0.9097    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983    1.2048   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143    0.3322   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917   -0.1568    2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232    1.3991    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045    1.5396    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -0.2233    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
 26 25  1  1
  7  2  1  0
 26  9  1  0
 17  5  1  0
 23 20  1  0
 26  6  1  0
 26 14  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  9 30  1  1
 10 31  1  1
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
M  END


  Mrv0541 04191212152D          

 26 31  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4435    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    0.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8374   -1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8374   -2.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -2.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 11  1  0  0  0  0
 15  1  1  0  0  0  0
  2 16  1  0  0  0  0
  1  6  2  0  0  0  0
  2  1  1  0  0  0  0
  5  2  2  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
 10 13  1  0  0  0  0
 16 13  1  0  0  0  0
 16  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  1  0  0  0
 12 18  1  0  0  0  0
 13 14  1  1  0  0  0
 11 15  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
  8 19  1  6  0  0  0
  5 20  1  0  0  0  0
  7 20  1  6  0  0  0
  4 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014982

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
NETZHAKZCGBWSS-CEDHKZHLSA-N

> <FORMULA>
C21H27NO4

> <MOLECULAR_WEIGHT>
357.4434

> <EXACT_MASS>
357.194008357

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.590130717988316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-triene-10,14,17-triol

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.1929245480479358

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.494562775371193

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.453262323474163

> <JCHEM_PKA_STRONGEST_BASIC>
13.75291030808839

> <JCHEM_POLAR_SURFACE_AREA>
73.16000000000001

> <JCHEM_REFRACTIVITY>
96.9999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nalbuphine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014982
     RDKit          3D
Nalbuphine
 53 58  0  0  0  0  0  0  0  0999 V2000
    5.2912   -1.4565    1.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0482   -1.5834    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118   -2.7829    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654   -2.8930   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5274   -1.7798   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -0.6437    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -0.4893    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658    0.8521    1.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    1.5918    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9514    2.1700   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0704    1.3728   -0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469    2.2066   -1.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137    0.9048   -1.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.7225   -0.7888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3326    1.8622   -0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -0.4670   -0.9174 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1778   -1.8083   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -0.2609   -0.0003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    0.1865   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459    0.4053    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -0.8247    1.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5074   -0.9581    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2213    0.3888   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.3832    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769    0.5881    1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1825    0.6025    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8980   -2.2514    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786   -3.6210    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0204   -3.8200   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615    2.4121    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.1885   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6940    1.3035    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    3.0715   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.3611   -2.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330    0.1018   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    1.0184   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4298    2.2767   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887   -0.4422   -1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -2.4518   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079   -2.3726   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -0.6421   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081    1.1216   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    1.3293    0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5173   -0.5754    2.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -1.6662    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -1.8173   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575   -0.9097    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983    1.2048   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143    0.3322   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917   -0.1568    2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232    1.3991    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045    1.5396    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -0.2233    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
 26 25  1  1
  7  2  1  0
 26  9  1  0
 17  5  1  0
 23 20  1  0
 26  6  1  0
 26 14  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  9 30  1  1
 10 31  1  1
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667  -1.540   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.695   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.663   0.077   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.296  -2.629   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.296  -4.169   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.836  -2.629   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.836  -4.169   0.000  0.00  0.00           C+0
CONECT    1   15    6    2                                                  
CONECT    2   16    1    5                                                  
CONECT    3    4    6                                                       
CONECT    4    3    5   21                                                  
CONECT    5    2    4   20                                                  
CONECT    6    1    3                                                       
CONECT    7   16    8   20                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10   13    9                                                       
CONECT   11   13   12   15                                                  
CONECT   12   11   18   22                                                  
CONECT   13   11   10   16   14                                             
CONECT   14   13                                                            
CONECT   15    1   11                                                       
CONECT   16    2   13    7   17                                             
CONECT   17   16   18                                                       
CONECT   18   12   17                                                       
CONECT   19    8                                                            
CONECT   20    5    7                                                       
CONECT   21    4                                                            
CONECT   22   12   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23   26                                                       
CONECT   26   25   24                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

COMPND    HMDB0014982
HETATM    1  O1  UNL     1       5.291  -1.456   1.714  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.048  -1.583   1.115  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.612  -2.783   0.550  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.365  -2.893  -0.046  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.527  -1.780  -0.082  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.985  -0.644   0.474  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.193  -0.489   1.065  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.266   0.852   1.505  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.266   1.592   0.752  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.951   2.170  -0.423  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.070   1.373  -0.716  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.147   2.207  -1.701  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.414   0.905  -1.938  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.491   0.722  -0.789  1.00  0.00           C  
HETATM   15  O4  UNL     1      -0.333   1.862  -0.731  1.00  0.00           O  
HETATM   16  C12 UNL     1      -0.434  -0.467  -0.917  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.178  -1.808  -0.736  1.00  0.00           C  
HETATM   18  N1  UNL     1      -1.506  -0.261  -0.000  1.00  0.00           N  
HETATM   19  C14 UNL     1      -2.712   0.186  -0.662  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.846   0.405   0.302  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.254  -0.825   1.084  1.00  0.00           C  
HETATM   22  C17 UNL     1      -5.507  -0.958   0.279  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.221   0.389  -0.330  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.225   0.383   1.217  1.00  0.00           C  
HETATM   25  C20 UNL     1       0.177   0.588   1.632  1.00  0.00           C  
HETATM   26  C21 UNL     1       1.183   0.603   0.509  1.00  0.00           C  
HETATM   27  H1  UNL     1       5.898  -2.251   1.744  1.00  0.00           H  
HETATM   28  H2  UNL     1       4.279  -3.621   0.594  1.00  0.00           H  
HETATM   29  H3  UNL     1       2.020  -3.820  -0.487  1.00  0.00           H  
HETATM   30  H4  UNL     1       1.962   2.412   1.436  1.00  0.00           H  
HETATM   31  H5  UNL     1       3.388   3.189  -0.201  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.694   1.304   0.027  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.457   3.071  -1.640  1.00  0.00           H  
HETATM   34  H8  UNL     1       2.807   2.361  -2.577  1.00  0.00           H  
HETATM   35  H9  UNL     1       2.133   0.102  -2.099  1.00  0.00           H  
HETATM   36  H10 UNL     1       0.811   1.018  -2.858  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.430   2.277  -1.624  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.889  -0.442  -1.953  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.460  -2.452  -0.081  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.308  -2.373  -1.689  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.022  -0.642  -1.344  1.00  0.00           H  
HETATM   42  H16 UNL     1      -2.508   1.122  -1.191  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.752   1.329   0.929  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.517  -0.575   2.146  1.00  0.00           H  
HETATM   45  H19 UNL     1      -3.547  -1.666   1.040  1.00  0.00           H  
HETATM   46  H20 UNL     1      -5.454  -1.817  -0.438  1.00  0.00           H  
HETATM   47  H21 UNL     1      -6.457  -0.910   0.853  1.00  0.00           H  
HETATM   48  H22 UNL     1      -5.898   1.205  -0.021  1.00  0.00           H  
HETATM   49  H23 UNL     1      -5.214   0.332  -1.439  1.00  0.00           H  
HETATM   50  H24 UNL     1      -1.792  -0.157   2.033  1.00  0.00           H  
HETATM   51  H25 UNL     1      -1.723   1.399   1.195  1.00  0.00           H  
HETATM   52  H26 UNL     1       0.305   1.540   2.193  1.00  0.00           H  
HETATM   53  H27 UNL     1       0.477  -0.223   2.327  1.00  0.00           H  
CONECT    1    2   27
CONECT    2    3    3    7
CONECT    3    4   28
CONECT    4    5    5   29
CONECT    5    6   17
CONECT    6    7    7   26
CONECT    7    8
CONECT    8    9
CONECT    9   10   26   30
CONECT   10   11   12   31
CONECT   11   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   16   26
CONECT   15   37
CONECT   16   17   18   38
CONECT   17   39   40
CONECT   18   19   24
CONECT   19   20   41   42
CONECT   20   21   23   43
CONECT   21   22   44   45
CONECT   22   23   46   47
CONECT   23   48   49
CONECT   24   25   50   51
CONECT   25   26   52   53
END

HMDB0014982
     RDKit          3D
Nalbuphine
 53 58  0  0  0  0  0  0  0  0999 V2000
    5.2912   -1.4565    1.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0482   -1.5834    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6118   -2.7829    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654   -2.8930   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5274   -1.7798   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -0.6437    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -0.4893    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658    0.8521    1.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    1.5918    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9514    2.1700   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0704    1.3728   -0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469    2.2066   -1.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4137    0.9048   -1.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.7225   -0.7888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3326    1.8622   -0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -0.4670   -0.9174 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1778   -1.8083   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -0.2609   -0.0003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    0.1865   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459    0.4053    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -0.8247    1.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5074   -0.9581    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2213    0.3888   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.3832    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769    0.5881    1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1825    0.6025    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8980   -2.2514    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786   -3.6210    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0204   -3.8200   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615    2.4121    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.1885   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6940    1.3035    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    3.0715   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.3611   -2.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330    0.1018   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    1.0184   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4298    2.2767   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887   -0.4422   -1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -2.4518   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079   -2.3726   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -0.6421   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081    1.1216   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    1.3293    0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5173   -0.5754    2.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -1.6662    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -1.8173   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575   -0.9097    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983    1.2048   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143    0.3322   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917   -0.1568    2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232    1.3991    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045    1.5396    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -0.2233    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
 26 25  1  1
  7  2  1  0
 26  9  1  0
 17  5  1  0
 23 20  1  0
 26  6  1  0
 26 14  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  9 30  1  1
 10 31  1  1
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Cyclobutylmethyl-4,5alpha-epoxy-3,6alpha,14-morphinantriol	ChEBI
Nalbufina	ChEBI
Nalbuphinum	ChEBI
Intapan	Kegg
N-Cyclobutylmethyl-4,5a-epoxy-3,6a,14-morphinantriol	Generator
N-Cyclobutylmethyl-4,5α-epoxy-3,6α,14-morphinantriol	Generator
Nubain	HMDB
Nalbuphine serb brand	HMDB
Hydrochloride, nalbuphine	HMDB
Serb, nalbuphine	HMDB
Nalbuphine hydrochloride	HMDB
Nalbuphine serb	HMDB
SERB brand OF nalbuphine	HMDB

Chemical Formula

C₂₁H₂₇NO₄

Average Molecular Weight

357.4434

Monoisotopic Molecular Weight

357.194008357

IUPAC Name

(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-triene-10,14,17-triol

Traditional Name

nalbuphine

CAS Registry Number

20594-83-6

SMILES

O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5

InChI Identifier

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

InChI Key

NETZHAKZCGBWSS-CEDHKZHLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Tetralin
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Piperidine
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Ether
Oxacycle
Polyol
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:7454 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	230 °C (hydrochloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.09 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	180.817	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000776

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.09 g/L	ALOGPS
logP	2	ALOGPS
logP	1.19	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	13.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.402	31661259
DarkChem	[M-H]-	174.403	31661259
DeepCCS	[M+H]+	183.204	30932474
DeepCCS	[M-H]-	180.808	30932474
DeepCCS	[M-2H]-	214.613	30932474
DeepCCS	[M+Na]+	189.402	30932474
AllCCS	[M+H]+	185.9	32859911
AllCCS	[M+H-H2O]+	183.4	32859911
AllCCS	[M+NH4]+	188.1	32859911
AllCCS	[M+Na]+	188.8	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	186.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.05 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7268 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.82 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	147.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1166.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	177.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	331.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	328.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	655.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	691.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	844.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	487.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	390.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	155.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nalbuphine	O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	4006.8	Standard polar	33892256
Nalbuphine	O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	2976.4	Standard non polar	33892256
Nalbuphine	O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	3087.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nalbuphine,1TMS,isomer #1	C[Si](C)(C)O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	2889.1	Semi standard non polar	33892256
Nalbuphine,1TMS,isomer #2	C[Si](C)(C)O[C@@]12CC[C@H](O)[C@@H]3OC4=C(O)C=CC5=C4[C@@]31CCN(CC1CCC1)[C@@H]2C5	2877.2	Semi standard non polar	33892256
Nalbuphine,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O)CC[C@@]35O	2931.9	Semi standard non polar	33892256
Nalbuphine,2TMS,isomer #1	C[Si](C)(C)O[C@H]1CC[C@@]2(O[Si](C)(C)C)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	2820.9	Semi standard non polar	33892256
Nalbuphine,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)CC[C@@]35O	2890.3	Semi standard non polar	33892256
Nalbuphine,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O)CC[C@@]35O[Si](C)(C)C	2868.5	Semi standard non polar	33892256
Nalbuphine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)CC[C@@]35O[Si](C)(C)C	2871.6	Semi standard non polar	33892256
Nalbuphine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	3120.5	Semi standard non polar	33892256
Nalbuphine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@]12CC[C@H](O)[C@@H]3OC4=C(O)C=CC5=C4[C@@]31CCN(CC1CCC1)[C@@H]2C5	3114.8	Semi standard non polar	33892256
Nalbuphine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O)CC[C@@]35O	3166.5	Semi standard non polar	33892256
Nalbuphine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(O[Si](C)(C)C(C)(C)C)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5	3294.6	Semi standard non polar	33892256
Nalbuphine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]35O	3363.1	Semi standard non polar	33892256
Nalbuphine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O)CC[C@@]35O[Si](C)(C)C(C)(C)C	3354.9	Semi standard non polar	33892256
Nalbuphine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]35O[Si](C)(C)C(C)(C)C	3564.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9024000000-f340950b62bc62155aad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS (3 TMS) - 70eV, Positive	splash10-0a6r-7200190000-d65993f303318329695e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalbuphine GC-MS ("Nalbuphine,2TMS,#3" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalbuphine 35V, Positive-QTOF	splash10-052f-0019000000-d9843432af7f0b68c123	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 10V, Positive-QTOF	splash10-052f-2009000000-ebce756d2f09cd1910ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 20V, Positive-QTOF	splash10-014i-9007000000-bbd85f5711c7e46af99d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 40V, Positive-QTOF	splash10-014i-9000000000-915ad990f371c4dabcfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 10V, Negative-QTOF	splash10-0a4i-0019000000-540f9874c968fbe7262c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 20V, Negative-QTOF	splash10-052r-1039000000-aa9a27b2348aafb5a2e8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 40V, Negative-QTOF	splash10-05g3-3090000000-fe24dd502f436a5787fa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 10V, Positive-QTOF	splash10-0a4i-0009000000-9957b000ea8c41ed8257	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 20V, Positive-QTOF	splash10-0a4i-0009000000-f48c8684121f5d183a1c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 40V, Positive-QTOF	splash10-0zfr-0019000000-e87bebcd47bdb1e8e0a4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 10V, Negative-QTOF	splash10-0a4i-0009000000-66d5ef9d584e1b0274e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 20V, Negative-QTOF	splash10-0a4i-0009000000-66d5ef9d584e1b0274e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalbuphine 40V, Negative-QTOF	splash10-0a4i-0019000000-3615de25291d9c20f0e3	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nalbuphine Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00844	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00844	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00844

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470813

KEGG Compound ID

C07251

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nalbuphine

METLIN ID

Not Available

PubChem Compound

5311304

PDB ID

Not Available

ChEBI ID

7454

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [PubMed:10534607 ]

Enzymes

Enzyme Details

1. Delta-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:: OPRD1
Uniprot ID:: P41143
Molecular weight:: 40412.3

References

Chen JC, Smith ER, Cahill M, Cohen R, Fishman JB: The opioid receptor binding of dezocine, morphine, fentanyl, butorphanol and nalbuphine. Life Sci. 1993;52(4):389-96. [PubMed:8093631 ]
De Souza EB, Schmidt WK, Kuhar MJ: Nalbuphine: an autoradiographic opioid receptor binding profile in the central nervous system of an agonist/antagonist analgesic. J Pharmacol Exp Ther. 1988 Jan;244(1):391-402. [PubMed:2826773 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Mu-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:: OPRM1
Uniprot ID:: P35372
Molecular weight:: 44778.9

References

Kishioka S, Ko MC, Woods JH: Diltiazem enhances the analgesic but not the respiratory depressant effects of morphine in rhesus monkeys. Eur J Pharmacol. 2000 May 26;397(1):85-92. [PubMed:10844102 ]
Hoehe M, Duka T: Opiates increase plasma catecholamines in humans. Psychoneuroendocrinology. 1993;18(2):141-8. [PubMed:8388112 ]
Zernig G, Lewis JW, Woods JH: Clocinnamox inhibits the intravenous self-administration of opioid agonists in rhesus monkeys: comparison with effects on opioid agonist-mediated antinociception. Psychopharmacology (Berl). 1997 Feb;129(3):233-42. [PubMed:9084061 ]
Picker MJ: Discriminative stimulus effects of the mixed-opioid agonist/antagonist dezocine: cross-substitution by mu and delta opioid agonists. J Pharmacol Exp Ther. 1997 Dec;283(3):1009-17. [PubMed:9399970 ]
McNicol ED, Boyce D, Schumann R, Carr DB: Mu-opioid antagonists for opioid-induced bowel dysfunction. Cochrane Database Syst Rev. 2008 Apr 16;(2):CD006332. doi: 10.1002/14651858.CD006332.pub2. [PubMed:18425947 ]
Tao PL, Liang KW, Sung WY, Wu YT, Huang EY: Nalbuphine is effective in decreasing the rewarding effect induced by morphine in rats. Drug Alcohol Depend. 2006 Sep 15;84(2):175-81. Epub 2006 Mar 6. [PubMed:16517095 ]
Smith MA, Greene-Naples JL, Lyle MA, Iordanou JC, Felder JN: The effects of repeated opioid administration on locomotor activity: I. Opposing actions of mu and kappa receptors. J Pharmacol Exp Ther. 2009 Aug;330(2):468-75. doi: 10.1124/jpet.108.150011. Epub 2009 Apr 29. [PubMed:19403853 ]
Mello NK, Mendelson JH, Sholar MB, Jaszyna-Gasior M, Goletiani N, Siegel AJ: Effects of the mixed mu/kappa opioid nalbuphine on cocaine-induced changes in subjective and cardiovascular responses in men. Neuropsychopharmacology. 2005 Mar;30(3):618-32. [PubMed:15602503 ]
Meerpohl JJ, Timmer A: [News from the cochrane library: mu opioid antagonists for opioid-induced bowel dysfunction]. Z Gastroenterol. 2008 Sep;46(9):917-21. doi: 10.1055/s-2008-1027720. Epub 2008 Sep 22. [PubMed:18810678 ]
Peng X, Knapp BI, Bidlack JM, Neumeyer JL: Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at mu, delta, and kappa opioid receptors. J Med Chem. 2007 May 3;50(9):2254-8. Epub 2007 Apr 4. [PubMed:17407276 ]

Enzyme Details

3. Kappa-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:: OPRK1
Uniprot ID:: P41145
Molecular weight:: 42644.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Hoehe M, Duka T: Opiates increase plasma catecholamines in humans. Psychoneuroendocrinology. 1993;18(2):141-8. [PubMed:8388112 ]
Chen SL, Huang EY, Chow LH, Tao PL: Dextromethorphan differentially affects opioid antinociception in rats. Br J Pharmacol. 2005 Feb;144(3):400-4. [PubMed:15655510 ]
Tao PL, Liang KW, Sung WY, Wu YT, Huang EY: Nalbuphine is effective in decreasing the rewarding effect induced by morphine in rats. Drug Alcohol Depend. 2006 Sep 15;84(2):175-81. Epub 2006 Mar 6. [PubMed:16517095 ]
Smith MA, Greene-Naples JL, Lyle MA, Iordanou JC, Felder JN: The effects of repeated opioid administration on locomotor activity: I. Opposing actions of mu and kappa receptors. J Pharmacol Exp Ther. 2009 Aug;330(2):468-75. doi: 10.1124/jpet.108.150011. Epub 2009 Apr 29. [PubMed:19403853 ]
Mello NK, Mendelson JH, Sholar MB, Jaszyna-Gasior M, Goletiani N, Siegel AJ: Effects of the mixed mu/kappa opioid nalbuphine on cocaine-induced changes in subjective and cardiovascular responses in men. Neuropsychopharmacology. 2005 Mar;30(3):618-32. [PubMed:15602503 ]
Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [PubMed:10534607 ]
Peng X, Knapp BI, Bidlack JM, Neumeyer JL: Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at mu, delta, and kappa opioid receptors. J Med Chem. 2007 May 3;50(9):2254-8. Epub 2007 Apr 4. [PubMed:17407276 ]

Showing metabocard for Nalbuphine (HMDB0014982)

MOL for HMDB0014982 (Nalbuphine)

3D MOL for HMDB0014982 (Nalbuphine)

3D SDF for HMDB0014982 (Nalbuphine)

3D-SDF for HMDB0014982 (Nalbuphine)

PDB for HMDB0014982 (Nalbuphine)

3D PDB for HMDB0014982 (Nalbuphine)

SMILES for HMDB0014982 (Nalbuphine)

INCHI for HMDB0014982 (Nalbuphine)

Structure for HMDB0014982 (Nalbuphine)

3D Structure for HMDB0014982 (Nalbuphine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References