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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 02:51:44 UTC

HMDB ID

HMDB0014749

Secondary Accession Numbers

HMDB14749

Metabolite Identification

Common Name

Butorphanol

Description

Butorphanol is only found in individuals that have used or taken this drug. It is a synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain. [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. Butorphanol is a mixed agonist-antagonist that exerts antagonistic or partially antagonistic effects at mu opiate receptor sites, but is thought to exert its agonistic effects principally at the kappa and sigma opiate receptors.

Structure

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

611
  Mrv0541 02231214482D          

 25 29  0  0  1  0            999 V2000
    6.4350   -0.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -1.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3724    0.1709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062   -1.0591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7205   -0.6466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7205    0.1784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8386   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929   -1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713   -1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7695   -0.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062    0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336   -2.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916    0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440    0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9309    1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071    1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878    2.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    2.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067   -0.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067    0.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    0.7498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  1  0  0  0
  2 23  1  0  0  0  0
  3  6  1  0  0  0  0
  3 11  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  6  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 12  1  0  0  0  0
  6 25  1  6  0  0  0
  7 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 10 20  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  1  0  0  0  0
 20 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END

HMDB0014749
     RDKit          3D
Butorphanol
 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.8356    2.2084    2.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285    2.0645    1.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    3.1664    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6961    2.9711    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369    1.6625    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    0.5727    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490    0.7937    1.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4546   -0.7976    0.3515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6765   -1.6486    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -2.5746   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1413   -1.8061   -2.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216   -0.6411   -2.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990   -0.8744   -0.7864 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1386   -2.1071   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.1502   -0.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0443    1.5490   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -0.2048    0.6622 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456   -0.7623    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5796    0.1995   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    1.3669    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516    1.0711    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9882   -0.3115    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978   -0.6775    1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534   -1.2797    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6768    2.2353    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856    4.1746    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167    3.8146    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452   -0.0369    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683   -2.2245    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -1.0028   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -3.4317   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5199   -3.0258   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -2.5035   -3.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -1.3748   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -0.6266   -2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328    0.3382   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -2.2807   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980    0.0800   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    2.1836    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.9677   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.6241   -0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -1.2033    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068    0.5573   -1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.3639    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.2340    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9190    1.0467    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    1.6289   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9782   -1.0889    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -0.6043   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.1714    2.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -1.4184    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -1.0541    2.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -2.3865    1.5229 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
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  0
  7  2  1  0
 13  8  1  0
 22 19  1  0
 16  5  1  0
 24  8  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
M  END

611
  Mrv0541 02231214482D          

 25 29  0  0  1  0            999 V2000
    6.4350   -0.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -1.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3724    0.1709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062   -1.0591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7205   -0.6466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7205    0.1784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8386   -0.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929   -1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713   -1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7695   -0.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062    0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336   -2.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -1.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916    0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440    0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9309    1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071    1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878    2.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    2.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067   -0.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067    0.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    0.7498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  1  0  0  0
  2 23  1  0  0  0  0
  3  6  1  0  0  0  0
  3 11  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  6  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 12  1  0  0  0  0
  6 25  1  6  0  0  0
  7 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 10 20  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  1  0  0  0  0
 20 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014749

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21+/m0/s1

> <INCHI_KEY>
IFKLAQQSCNILHL-PWRODBHTSA-N

> <FORMULA>
C21H29NO2

> <MOLECULAR_WEIGHT>
327.4605

> <EXACT_MASS>
327.219829177

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.93936033693934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
2.8903292922420443

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.72921326420759

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.864342496681376

> <JCHEM_PKA_STRONGEST_BASIC>
10.70358494827157

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
95.921

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butorphanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014749
     RDKit          3D
Butorphanol
 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.8356    2.2084    2.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285    2.0645    1.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    3.1664    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6961    2.9711    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369    1.6625    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    0.5727    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490    0.7937    1.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4546   -0.7976    0.3515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6765   -1.6486    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -2.5746   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1413   -1.8061   -2.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216   -0.6411   -2.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990   -0.8744   -0.7864 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1386   -2.1071   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.1502   -0.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0443    1.5490   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -0.2048    0.6622 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456   -0.7623    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5796    0.1995   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    1.3669    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516    1.0711    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9882   -0.3115    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978   -0.6775    1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534   -1.2797    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6768    2.2353    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856    4.1746    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167    3.8146    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452   -0.0369    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683   -2.2245    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -1.0028   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -3.4317   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5199   -3.0258   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -2.5035   -3.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -1.3748   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -0.6266   -2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328    0.3382   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -2.2807   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980    0.0800   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    2.1836    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.9677   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.6241   -0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -1.2033    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068    0.5573   -1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.3639    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.2340    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9190    1.0467    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    1.6289   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9782   -1.0889    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -0.6043   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.1714    2.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -1.4184    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -1.0541    2.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -2.3865    1.5229 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
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  0
  7  2  1  0
 13  8  1  0
 22 19  1  0
 16  5  1  0
 24  8  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 611                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.012  -0.437   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.909  -2.014   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      10.028   0.319   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.345  -1.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.678  -1.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.678   0.333   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.032  -1.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.320  -3.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.080  -1.987   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.011  -1.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.903  -0.182   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.345   1.103   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.703  -4.393   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.092  -3.591   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.011   0.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.349   1.825   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.204   2.856   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.667   2.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.124   4.393   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.635  -2.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.586   4.313   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.635   1.156   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.239  -1.239   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.239   0.365   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      11.294   1.400   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   23                                                            
CONECT    3    6   11   16                                                  
CONECT    4    5    7    8   10                                             
CONECT    5    1    4    6    9                                             
CONECT    6    3    5   12   25                                             
CONECT    7    4   11                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10    4   15   20                                                  
CONECT   11    3    7                                                       
CONECT   12    6   15                                                       
CONECT   13    8   14                                                       
CONECT   14    9   13                                                       
CONECT   15   10   12   22                                                  
CONECT   16    3   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   21                                                       
CONECT   19   17   21                                                       
CONECT   20   10   23                                                       
CONECT   21   18   19                                                       
CONECT   22   15   24                                                       
CONECT   23    2   20   24                                                  
CONECT   24   22   23                                                       
CONECT   25    6                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0014749
HETATM    1  O1  UNL     1      -4.836   2.208   2.160  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.629   2.065   1.493  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.893   3.166   1.059  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.696   2.971   0.400  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.237   1.662   0.177  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.933   0.573   0.590  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.149   0.794   1.258  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.455  -0.798   0.351  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.676  -1.649   0.077  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.506  -2.575  -1.086  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.141  -1.806  -2.328  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.222  -0.641  -2.088  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.499  -0.874  -0.786  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.139  -2.107  -0.855  1.00  0.00           O  
HETATM   15  C13 UNL     1       0.580   0.150  -0.506  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.044   1.549  -0.526  1.00  0.00           C  
HETATM   17  N1  UNL     1       1.268  -0.205   0.662  1.00  0.00           N  
HETATM   18  C15 UNL     1       2.546  -0.762   0.411  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.580   0.200  -0.129  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.880   1.367   0.780  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.352   1.071   0.620  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.988  -0.311   0.139  1.00  0.00           C  
HETATM   23  C20 UNL     1       0.598  -0.678   1.792  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.753  -1.280   1.598  1.00  0.00           C  
HETATM   25  H1  UNL     1      -5.677   2.235   1.590  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.286   4.175   1.253  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.117   3.815   0.057  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.745  -0.037   1.609  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.968  -2.224   0.968  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.566  -1.003  -0.184  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.840  -3.432  -0.873  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.520  -3.026  -1.271  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.774  -2.504  -3.104  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.091  -1.375  -2.739  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.465  -0.627  -2.898  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.733   0.338  -2.091  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.417  -2.281  -1.800  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.298   0.080  -1.372  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.773   2.184   0.032  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.000   1.968  -1.559  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.519  -1.624  -0.319  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.914  -1.203   1.364  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.407   0.557  -1.164  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.647   2.364   0.371  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.588   1.234   1.844  1.00  0.00           H  
HETATM   46  H22 UNL     1       5.919   1.047   1.576  1.00  0.00           H  
HETATM   47  H23 UNL     1       5.860   1.629  -0.213  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.978  -1.089   0.919  1.00  0.00           H  
HETATM   49  H25 UNL     1       5.521  -0.604  -0.803  1.00  0.00           H  
HETATM   50  H26 UNL     1       0.491   0.171   2.519  1.00  0.00           H  
HETATM   51  H27 UNL     1       1.233  -1.418   2.321  1.00  0.00           H  
HETATM   52  H28 UNL     1      -1.423  -1.054   2.450  1.00  0.00           H  
HETATM   53  H29 UNL     1      -0.711  -2.387   1.523  1.00  0.00           H  
CONECT    1    2   25
CONECT    2    3    3    7
CONECT    3    4   26
CONECT    4    5    5   27
CONECT    5    6   16
CONECT    6    7    7    8
CONECT    7   28
CONECT    8    9   13   24
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   15
CONECT   14   37
CONECT   15   16   17   38
CONECT   16   39   40
CONECT   17   18   23
CONECT   18   19   41   42
CONECT   19   20   22   43
CONECT   20   21   44   45
CONECT   21   22   46   47
CONECT   22   48   49
CONECT   23   24   50   51
CONECT   24   52   53
END

HMDB0014749
     RDKit          3D
Butorphanol
 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.8356    2.2084    2.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285    2.0645    1.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    3.1664    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6961    2.9711    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369    1.6625    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    0.5727    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490    0.7937    1.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4546   -0.7976    0.3515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6765   -1.6486    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -2.5746   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1413   -1.8061   -2.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216   -0.6411   -2.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990   -0.8744   -0.7864 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1386   -2.1071   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.1502   -0.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0443    1.5490   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -0.2048    0.6622 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456   -0.7623    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5796    0.1995   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    1.3669    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516    1.0711    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9882   -0.3115    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978   -0.6775    1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534   -1.2797    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6768    2.2353    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856    4.1746    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167    3.8146    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452   -0.0369    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683   -2.2245    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -1.0028   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -3.4317   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5199   -3.0258   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -2.5035   -3.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -1.3748   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -0.6266   -2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328    0.3382   -2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -2.2807   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980    0.0800   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    2.1836    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.9677   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -1.6241   -0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -1.2033    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068    0.5573   -1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.3639    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.2340    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9190    1.0467    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    1.6289   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9782   -1.0889    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215   -0.6043   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.1714    2.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -1.4184    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -1.0541    2.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -2.3865    1.5229 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
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  0
  7  2  1  0
 13  8  1  0
 22 19  1  0
 16  5  1  0
 24  8  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Butorfanol	HMDB
Butorphanol tartrate	HMDB
17-(Cyclobutylmethyl)morphinan-3,14-diol	HMDB
Apo-butorphanol	HMDB
Apotex brand OF butorphanol tartrate	HMDB
Beforal	HMDB
Bristol-myers squibb brand OF butorphanol tartrate	HMDB
Cephalon brand OF butorphanol tartrate	HMDB
Dolorex	HMDB
Fort dodge brand OF butorphanol tartrate	HMDB
Geneva brand OF butorphanol tartrate	HMDB
Intervet brand OF butorphanol tartrate	HMDB
Moradol	HMDB
Stadol	HMDB
Stadol NS	HMDB
Torbugesic	HMDB

Chemical Formula

C₂₁H₂₉NO₂

Average Molecular Weight

327.4605

Monoisotopic Molecular Weight

327.219829177

IUPAC Name

(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol

Traditional Name

butorphanol

CAS Registry Number

58786-99-5

SMILES

[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1

InChI Identifier

InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21+/m0/s1

InChI Key

IFKLAQQSCNILHL-PWRODBHTSA-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
Benzazocine
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014749)

Source

Exogenous

Exogenous (HMDB: HMDB0014749)

Process

Not Available

Role

Industrial application

Kappa-opioid receptor agonist (HMDB: HMDB0014749)
Mu-opioid receptor agonist (HMDB: HMDB0014749)
Opioid analgesic (HMDB: HMDB0014749)

Pharmaceutical industry

Antitussive (HMDB: HMDB0014749)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.16 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.65	ALOGPS
logP	2.89	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.86	ChemAxon
pKa (Strongest Basic)	10.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.92 m³·mol⁻¹	ChemAxon
Polarizability	37.94 Å³	ChemAxon
Number of Rings	5	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]+	176.022	31661259
DarkChem	[M-H]-	171.813	31661259
DeepCCS	[M-2H]-	215.453	30932474
DeepCCS	[M+Na]+	190.427	30932474
AllCCS	[M+H]+	181.6	32859911
AllCCS	[M+H-H2O]+	178.9	32859911
AllCCS	[M+NH4]+	184.2	32859911
AllCCS	[M+Na]+	184.9	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.4	32859911
AllCCS	[M+HCOO]-	183.5	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.	4.0 minutes	32390414
Predicted by Siyang on May 30, 2022	10.129 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.45 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	95.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1338.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	167.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	395.8 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	365.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	684.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	825.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	326.8 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	907.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	540.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	330.8 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	105.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butorphanol	[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1	3766.4	Standard polar	33892256
Butorphanol	[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1	2846.2	Standard non polar	33892256
Butorphanol	[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1	2871.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butorphanol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@@]4(CCCC[C@@]34O)C2=C1	2719.6	Semi standard non polar	33892256
Butorphanol,1TMS,isomer #2	C[Si](C)(C)O[C@@]12CCCC[C@@]13CCN(CC1CCC1)[C@@H]2CC1=CC=C(O)C=C13	2695.2	Semi standard non polar	33892256
Butorphanol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@@]4(CCCC[C@@]34O[Si](C)(C)C)C2=C1	2684.1	Semi standard non polar	33892256
Butorphanol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@@]4(CCCC[C@@]34O)C2=C1	2964.1	Semi standard non polar	33892256
Butorphanol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@]12CCCC[C@@]13CCN(CC1CCC1)[C@@H]2CC1=CC=C(O)C=C13	2948.9	Semi standard non polar	33892256
Butorphanol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@@]4(CCCC[C@@]34O[Si](C)(C)C(C)(C)C)C2=C1	3166.2	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 - Butorphanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05c5-4090000000-ff08db00ae2474f6b4a5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-6004900000-19e8948f63ea068f317c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butorphanol GC-MS ("Butorphanol,1TMS,#2" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 10V, Positive-QTOF	splash10-0400-3009000000-2dca83671d56d098a9c9	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 20V, Positive-QTOF	splash10-02t9-9024000000-f37bfb8ff0e2cf917155	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 40V, Positive-QTOF	splash10-014i-9000000000-b3868f9e593caf3b586b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 10V, Negative-QTOF	splash10-004i-0029000000-d2856cd83df5e8d33b65	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 20V, Negative-QTOF	splash10-0a6r-2098000000-a2f7eacf8c80072ad5b6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 40V, Negative-QTOF	splash10-0a4l-4090000000-37ed14b31b49d2194700	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 10V, Positive-QTOF	splash10-004i-0009000000-8ed73bd9ae49e58d578e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 20V, Positive-QTOF	splash10-004i-0009000000-3cb1bcbf15b91d40d3a0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 40V, Positive-QTOF	splash10-017l-5094000000-f351e63d912694f61c8f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 10V, Negative-QTOF	splash10-004i-0009000000-ad4847b3b72e4c91ee0a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 20V, Negative-QTOF	splash10-004i-0009000000-ad4847b3b72e4c91ee0a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butorphanol 40V, Negative-QTOF	splash10-0ab9-1957000000-6d5cd344c3106be1f9e2	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00611	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00611	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

DB00611

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16735714

KEGG Compound ID

C06863

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butorphanol

METLIN ID

Not Available

PubChem Compound

5361092

PDB ID

Not Available

ChEBI ID

3242

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

Fan LW, Tanaka S, Tien LT, Ma T, Rockhold RW, Ho IK: Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain. Brain Res Bull. 2002 Jun;58(2):149-60. [PubMed:12127012 ]
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

Fan LW, Tanaka S, Tien LT, Ma T, Rockhold RW, Ho IK: Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain. Brain Res Bull. 2002 Jun;58(2):149-60. [PubMed:12127012 ]
Fan LW, Tanaka S, Park Y, Sasaki K, Ma T, Tien LT, Rockhold RW, Ho IK: Butorphanol dependence and withdrawal decrease hippocampal kappa 2-opioid receptor binding. Brain Res. 2002 Dec 27;958(2):277-90. [PubMed:12470863 ]
Commiskey S, Fan LW, Ho IK, Rockhold RW: Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16. Epub 2005 Jun 8. [PubMed:15942128 ]
Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334 ]
Wakabayashi H, Tokuyama S, Ho IK: Simultaneous measurement of biogenic amines and their metabolites in rat brain regions after acute administration of and abrupt withdrawal from butorphanol or morphine. Neurochem Res. 1995 Oct;20(10):1179-85. [PubMed:8746803 ]
Narita M, Feng Y, Makimura M, Hoskins B, Ho IK: Repeated administration of opioids alters characteristics of membrane-bound phorbol ester binding in rat brain. Eur J Pharmacol. 1994 Dec 27;271(2-3):547-50. [PubMed:7705457 ]
Walsh SL, Chausmer AE, Strain EC, Bigelow GE: Evaluation of the mu and kappa opioid actions of butorphanol in humans through differential naltrexone blockade. Psychopharmacology (Berl). 2008 Jan;196(1):143-55. Epub 2007 Oct 2. [PubMed:17909753 ]
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

Vivian JA, DeYoung MB, Sumpter TL, Traynor JR, Lewis JW, Woods JH: kappa-Opioid receptor effects of butorphanol in rhesus monkeys. J Pharmacol Exp Ther. 1999 Jul;290(1):259-65. [PubMed:10381785 ]
Fan LW, Tanaka S, Tien LT, Ma T, Rockhold RW, Ho IK: Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain. Brain Res Bull. 2002 Jun;58(2):149-60. [PubMed:12127012 ]
Fan LW, Tanaka S, Park Y, Sasaki K, Ma T, Tien LT, Rockhold RW, Ho IK: Butorphanol dependence and withdrawal decrease hippocampal kappa 2-opioid receptor binding. Brain Res. 2002 Dec 27;958(2):277-90. [PubMed:12470863 ]
Commiskey S, Fan LW, Ho IK, Rockhold RW: Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16. Epub 2005 Jun 8. [PubMed:15942128 ]
Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334 ]
Wakabayashi H, Tokuyama S, Ho IK: Simultaneous measurement of biogenic amines and their metabolites in rat brain regions after acute administration of and abrupt withdrawal from butorphanol or morphine. Neurochem Res. 1995 Oct;20(10):1179-85. [PubMed:8746803 ]
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 ]
Narita M, Feng Y, Makimura M, Hoskins B, Ho IK: Repeated administration of opioids alters characteristics of membrane-bound phorbol ester binding in rat brain. Eur J Pharmacol. 1994 Dec 27;271(2-3):547-50. [PubMed:7705457 ]
Walsh SL, Chausmer AE, Strain EC, Bigelow GE: Evaluation of the mu and kappa opioid actions of butorphanol in humans through differential naltrexone blockade. Psychopharmacology (Berl). 2008 Jan;196(1):143-55. Epub 2007 Oct 2. [PubMed:17909753 ]

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

Vivian JA, DeYoung MB, Sumpter TL, Traynor JR, Lewis JW, Woods JH: kappa-Opioid receptor effects of butorphanol in rhesus monkeys. J Pharmacol Exp Ther. 1999 Jul;290(1):259-65. [PubMed:10381785 ]
Park Y, Jang CG, Ho IK, Ko KH: kappa-opioid agonist stimulated regional distribution of [(35)S]GTPgammas binding in butorphanol continuously infused rat. Brain Res Bull. 2000 May 1;52(1):17-20. [PubMed:10779697 ]
Fan LW, Tanaka S, Tien LT, Ma T, Rockhold RW, Ho IK: Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain. Brain Res Bull. 2002 Jun;58(2):149-60. [PubMed:12127012 ]
Fan LW, Tanaka S, Park Y, Sasaki K, Ma T, Tien LT, Rockhold RW, Ho IK: Butorphanol dependence and withdrawal decrease hippocampal kappa 2-opioid receptor binding. Brain Res. 2002 Dec 27;958(2):277-90. [PubMed:12470863 ]
Commiskey S, Fan LW, Ho IK, Rockhold RW: Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16. Epub 2005 Jun 8. [PubMed:15942128 ]
Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334 ]
Wakabayashi H, Tokuyama S, Ho IK: Simultaneous measurement of biogenic amines and their metabolites in rat brain regions after acute administration of and abrupt withdrawal from butorphanol or morphine. Neurochem Res. 1995 Oct;20(10):1179-85. [PubMed:8746803 ]
Narita M, Feng Y, Makimura M, Hoskins B, Ho IK: Repeated administration of opioids alters characteristics of membrane-bound phorbol ester binding in rat brain. Eur J Pharmacol. 1994 Dec 27;271(2-3):547-50. [PubMed:7705457 ]
Ohta S, Niwa M, Nozaki M, Tsurumi K, Shimonaka H, Tanahashi T, Uematsu H, Yamamoto M, Fujimura H: [Kappa-type opioid receptor in human placental membrane]. Masui. 1989 Oct;38(10):1293-300. [PubMed:2555580 ]
Walsh SL, Chausmer AE, Strain EC, Bigelow GE: Evaluation of the mu and kappa opioid actions of butorphanol in humans through differential naltrexone blockade. Psychopharmacology (Berl). 2008 Jan;196(1):143-55. Epub 2007 Oct 2. [PubMed:17909753 ]

Showing metabocard for Butorphanol (HMDB0014749)

MOL for HMDB0014749 (Butorphanol)

3D MOL for HMDB0014749 (Butorphanol)

3D SDF for HMDB0014749 (Butorphanol)

3D-SDF for HMDB0014749 (Butorphanol)

PDB for HMDB0014749 (Butorphanol)

3D PDB for HMDB0014749 (Butorphanol)

SMILES for HMDB0014749 (Butorphanol)

INCHI for HMDB0014749 (Butorphanol)

Structure for HMDB0014749 (Butorphanol)

3D Structure for HMDB0014749 (Butorphanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References