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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (16) Show 16 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 02:51:43 UTC

HMDB ID

HMDB0014727

Secondary Accession Numbers

HMDB14727

Metabolite Identification

Common Name

Lisuride

Description

Lisuride, also known as lisuridum or dopergine, belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline. Lisuride, sold under the brand names Dopergin, Proclacam, and Revanil, is an antiparkinson agent of the iso-ergoline class, chemically related to the dopaminergic ergoline Parkinson's drugs. Lisuride is a drug which is used for the management of parkinson's disease. Lisuride is used to lower prolactin and, in low doses, to prevent migraine attacks. Lisuride is a very strong basic compound (based on its pKa). Lisuride is not currently available in the US, as the drug was not a commercial success in comparison with other dopamine receptor agonist antiparkinsonian compounds. It is an antagonist at the serotonin 5-HT2B receptor. Bromination of lisuride gives bromerguride, which has a "[completely] reversed pharmacodynamic profile" compared to that of lisuride. GPCR oligomers are discrete entities and usually possess properties distinct from their parent monomeric receptors. Newer findings suggest the lack of psychedelic action arises from the phenomenon of biased agonism.

Structure

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

589
  Mrv0541 02231214472D          

 26 29  0  0  1  0            999 V2000
    4.5073    2.1324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985    0.4769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976    0.8924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9735   -2.9186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785    2.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -0.3821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2709   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6997   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136    0.4826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2578    0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6997   -1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709   -1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -2.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -0.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985   -2.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7177    0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3076   -2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136   -2.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945    1.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    1.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754    2.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3594    3.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5593   -0.0567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2  6  1  0  0  0  0
  2 10  1  0  0  0  0
  2 16  1  0  0  0  0
  9  3  1  6  0  0  0
  3 21  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 26  1  1  0  0  0
  7 12  1  0  0  0  0
  7 14  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 11 13  1  0  0  0  0
 11 17  2  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 15 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

HMDB0014727
     RDKit          3D
Lisuride
 51 54  0  0  0  0  0  0  0  0999 V2000
   -6.2077    0.8442    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2896   -0.2146    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0725   -0.3360    0.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321   -1.2708   -0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395   -2.6138   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    0.4549    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0453    1.2770    1.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100    0.4097    0.0233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.2557    0.4080 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5440    0.3533    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.5394    0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -0.3437    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6483   -1.3018    1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -2.0962    2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737   -1.9351    1.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680   -0.9830    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553   -0.5351   -0.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7051    0.4674   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.6892   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0791   -0.2213    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    1.6017   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    1.6286   -0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9129    1.6668   -1.4952 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    0.4386   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.1224   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3645    0.6868   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2064    0.7359    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    1.8622    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193    0.1401    2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7842   -1.1830    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0524   -1.4728   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658   -0.9847   -1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295   -2.4388    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837   -3.3344   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915   -2.9437    0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.2632   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    1.8597    1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474   -0.4137    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7035   -1.3995    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -2.8460    2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247   -2.5505    1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1281   -0.9301   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2161    1.0510   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958    2.6478   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1478    1.4888   -2.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    2.5775    0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.5178   -2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308   -0.4522   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.2887   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    3.1330   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    2.3259   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25  9  1  0
 22 11  1  0
 20 12  1  0
 20 16  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
  9 37  1  1
 10 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
M  END

589
  Mrv0541 02231214472D          

 26 29  0  0  1  0            999 V2000
    4.5073    2.1324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985    0.4769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976    0.8924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9735   -2.9186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785    2.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -0.3821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2709   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6997   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136    0.4826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2578    0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6997   -1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709   -1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852   -2.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -0.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985   -2.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7177    0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3076   -2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2578   -3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136   -2.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945    1.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    1.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754    2.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3594    3.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5593   -0.0567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2  6  1  0  0  0  0
  2 10  1  0  0  0  0
  2 16  1  0  0  0  0
  9  3  1  6  0  0  0
  3 21  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 26  1  1  0  0  0
  7 12  1  0  0  0  0
  7 14  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 11 13  1  0  0  0  0
 11 17  2  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 15 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014727

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC

> <INCHI_IDENTIFIER>
InChI=1S/C20H26N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25)/t14-,18+/m0/s1

> <INCHI_KEY>
BKRGVLQUQGGVSM-KBXCAEBGSA-N

> <FORMULA>
C20H26N4O

> <MOLECULAR_WEIGHT>
338.4466

> <EXACT_MASS>
338.210661474

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.80745333546789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3-diethyl-1-[(4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl]urea

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.1692287139999995

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.023161278725247

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.356023075539433

> <JCHEM_PKA_STRONGEST_BASIC>
6.875951361180381

> <JCHEM_POLAR_SURFACE_AREA>
51.370000000000005

> <JCHEM_REFRACTIVITY>
101.81210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lisuride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014727
     RDKit          3D
Lisuride
 51 54  0  0  0  0  0  0  0  0999 V2000
   -6.2077    0.8442    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2896   -0.2146    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0725   -0.3360    0.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321   -1.2708   -0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395   -2.6138   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    0.4549    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0453    1.2770    1.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100    0.4097    0.0233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.2557    0.4080 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5440    0.3533    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.5394    0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -0.3437    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6483   -1.3018    1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -2.0962    2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737   -1.9351    1.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680   -0.9830    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553   -0.5351   -0.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7051    0.4674   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.6892   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0791   -0.2213    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    1.6017   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    1.6286   -0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9129    1.6668   -1.4952 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    0.4386   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.1224   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3645    0.6868   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2064    0.7359    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    1.8622    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193    0.1401    2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7842   -1.1830    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0524   -1.4728   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658   -0.9847   -1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295   -2.4388    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837   -3.3344   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915   -2.9437    0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.2632   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    1.8597    1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474   -0.4137    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7035   -1.3995    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -2.8460    2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247   -2.5505    1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1281   -0.9301   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2161    1.0510   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958    2.6478   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1478    1.4888   -2.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    2.5775    0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.5178   -2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308   -0.4522   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.2887   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    3.1330   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    2.3259   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25  9  1  0
 22 11  1  0
 20 12  1  0
 20 16  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
  9 37  1  1
 10 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 589                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.414   3.980   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      11.197   0.890   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       7.089   1.666   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      13.017  -5.448   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.747   3.970   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.172  -0.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.839  -1.483   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.506  -1.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.425   0.901   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.815   1.703   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.506  -3.023   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.839  -3.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.172  -3.793   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.438  -0.703   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.197  -5.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.540   1.645   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.641  -4.050   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.438  -3.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.815  -6.209   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.425  -5.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.083   3.206   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.416   3.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.741   5.510   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   3.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.404   6.275   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      12.244  -0.106   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    6   10   16                                                  
CONECT    3    9   21                                                       
CONECT    4   15   17                                                       
CONECT    5   21   22   23                                                  
CONECT    6    2    7    8   26                                             
CONECT    7    6   12   14                                                  
CONECT    8    6   11                                                       
CONECT    9    3   10   14                                                  
CONECT   10    2    9                                                       
CONECT   11    8   13   17                                                  
CONECT   12    7   13   18                                                  
CONECT   13   11   12   15                                                  
CONECT   14    7    9                                                       
CONECT   15    4   13   19                                                  
CONECT   16    2                                                            
CONECT   17    4   11                                                       
CONECT   18   12   20                                                       
CONECT   19   15   20                                                       
CONECT   20   18   19                                                       
CONECT   21    1    3    5                                                  
CONECT   22    5   24                                                       
CONECT   23    5   25                                                       
CONECT   24   22                                                            
CONECT   25   23                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0014727
HETATM    1  C1  UNL     1      -6.208   0.844   0.572  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.290  -0.215   1.173  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.072  -0.336   0.399  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.032  -1.271  -0.692  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.540  -2.614  -0.162  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.964   0.455   0.722  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.045   1.277   1.694  1.00  0.00           O  
HETATM    8  N2  UNL     1      -1.710   0.410   0.023  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.603   1.256   0.408  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.544   0.353   0.817  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.752   0.539   0.356  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.826  -0.344   0.772  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.648  -1.302   1.747  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.745  -2.096   2.086  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.974  -1.935   1.470  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.168  -0.983   0.495  1.00  0.00           C  
HETATM   17  N3  UNL     1       6.155  -0.535  -0.300  1.00  0.00           N  
HETATM   18  C14 UNL     1       5.705   0.467  -1.079  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.336   0.689  -0.775  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.079  -0.221   0.183  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.340   1.602  -1.280  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.052   1.629  -0.579  1.00  0.00           C  
HETATM   23  N4  UNL     1       0.913   1.667  -1.495  1.00  0.00           N  
HETATM   24  C19 UNL     1       0.648   0.439  -2.157  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.223   2.122  -0.742  1.00  0.00           C  
HETATM   26  H1  UNL     1      -6.364   0.687  -0.511  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.206   0.736   1.078  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.864   1.862   0.817  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.019   0.140   2.191  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.784  -1.183   1.249  1.00  0.00           H  
HETATM   31  H6  UNL     1      -5.052  -1.473  -1.104  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.366  -0.985  -1.522  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.529  -2.439   0.255  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.484  -3.334  -0.994  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.192  -2.944   0.672  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.637  -0.263  -0.772  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.937   1.860   1.276  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.247  -0.414   1.493  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.704  -1.399   2.200  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.590  -2.846   2.855  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.825  -2.551   1.732  1.00  0.00           H  
HETATM   42  H17 UNL     1       7.128  -0.930  -0.291  1.00  0.00           H  
HETATM   43  H18 UNL     1       6.216   1.051  -1.823  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.796   2.648  -1.201  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.148   1.489  -2.382  1.00  0.00           H  
HETATM   46  H21 UNL     1       1.985   2.577   0.038  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.352   0.518  -2.629  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.631  -0.452  -1.506  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.347   0.289  -3.030  1.00  0.00           H  
HETATM   50  H25 UNL     1       0.035   3.133  -0.310  1.00  0.00           H  
HETATM   51  H26 UNL     1      -1.062   2.326  -1.440  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    6
CONECT    4    5   31   32
CONECT    5   33   34   35
CONECT    6    7    7    8
CONECT    8    9   36
CONECT    9   10   25   37
CONECT   10   11   11   38
CONECT   11   12   22
CONECT   12   13   13   20
CONECT   13   14   39
CONECT   14   15   15   40
CONECT   15   16   41
CONECT   16   17   20   20
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20   21
CONECT   21   22   44   45
CONECT   22   23   46
CONECT   23   24   25
CONECT   24   47   48   49
CONECT   25   50   51
END

HMDB0014727
     RDKit          3D
Lisuride
 51 54  0  0  0  0  0  0  0  0999 V2000
   -6.2077    0.8442    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2896   -0.2146    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0725   -0.3360    0.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321   -1.2708   -0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5395   -2.6138   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    0.4549    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0453    1.2770    1.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100    0.4097    0.0233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030    1.2557    0.4080 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5440    0.3533    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.5394    0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -0.3437    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6483   -1.3018    1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -2.0962    2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737   -1.9351    1.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680   -0.9830    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553   -0.5351   -0.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7051    0.4674   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.6892   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0791   -0.2213    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    1.6017   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    1.6286   -0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9129    1.6668   -1.4952 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    0.4386   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.1224   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3645    0.6868   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2064    0.7359    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    1.8622    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193    0.1401    2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0524   -1.4728   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658   -0.9847   -1.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295   -2.4388    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837   -3.3344   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915   -2.9437    0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.2632   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    1.8597    1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474   -0.4137    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7035   -1.3995    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -2.8460    2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247   -2.5505    1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1281   -0.9301   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2161    1.0510   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958    2.6478   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1478    1.4888   -2.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    2.5775    0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.5178   -2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308   -0.4522   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.2887   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    3.1330   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    2.3259   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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 25  9  1  0
 22 11  1  0
 20 12  1  0
 20 16  2  0
  1 26  1  0
  1 27  1  0
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  5 34  1  0
  5 35  1  0
  8 36  1  0
  9 37  1  1
 10 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lisurida	ChEBI
Lisuridum	ChEBI
N'-((8alpha)-9,10-didehydro-6-methylergolin-8-yl)-N,N-diethylurea	ChEBI
N'-((8a)-9,10-didehydro-6-methylergolin-8-yl)-N,N-diethylurea	Generator
N'-((8α)-9,10-didehydro-6-methylergolin-8-yl)-N,N-diethylurea	Generator
Dopergine	HMDB
Lisuride hydrochloride	HMDB
Lisuride phosphate (1:1)	HMDB
Cuvalit	HMDB
IPRAD brand OF lisuride maleate	HMDB
Lisuride mesylate	HMDB
Mesylate, lisuride	HMDB
Methylergol carbamide	HMDB
Hydrogen maleate, lysuride	HMDB
Lisuride maleate	HMDB
Lisuride maleate (1:1)	HMDB
Lisuride maleate, (8beta)-isomer	HMDB
Lisuride, (8alpha)-(+-)-isomer	HMDB
Lysenyl	HMDB
Lysuride hydrogen maleate	HMDB
Maleate, lisuride	HMDB
Revanil	HMDB
Roche brand OF lisuride maleate	HMDB
Schering brand 2 OF lisuride maleate	HMDB
Arolac	HMDB
Carbamide, methylergol	HMDB
Dopergin	HMDB
Hydrochloride, lisuride	HMDB
Lysurid	HMDB
Schering brand 1 OF lisuride maleate	HMDB

Chemical Formula

C₂₀H₂₆N₄O

Average Molecular Weight

338.4466

Monoisotopic Molecular Weight

338.210661474

IUPAC Name

3,3-diethyl-1-[(4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl]urea

Traditional Name

lisuride

CAS Registry Number

18016-80-3

SMILES

[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC

InChI Identifier

InChI=1S/C20H26N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25)/t14-,18+/m0/s1

InChI Key

BKRGVLQUQGGVSM-KBXCAEBGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Indoloquinolines

Direct Parent

Indoloquinolines

Alternative Parents

Substituents

Ergoline skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Alkaloid or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Carbonic acid derivative
Urea
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:51164 )

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: HMDB0014727)

Source

Exogenous

Exogenous (HMDB: HMDB0014727)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.37	ALOGPS
logP	2.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.36	ChemAxon
pKa (Strongest Basic)	6.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	51.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.81 m³·mol⁻¹	ChemAxon
Polarizability	38.81 Å³	ChemAxon
Number of Rings	4	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]+	180.51	31661259
DarkChem	[M-H]-	177.577	31661259
DeepCCS	[M-2H]-	217.897	30932474
DeepCCS	[M+Na]+	192.901	30932474
AllCCS	[M+H]+	183.7	32859911
AllCCS	[M+H-H2O]+	180.8	32859911
AllCCS	[M+NH4]+	186.5	32859911
AllCCS	[M+Na]+	187.2	32859911
AllCCS	[M-H]-	188.2	32859911
AllCCS	[M+Na-2H]-	188.1	32859911
AllCCS	[M+HCOO]-	188.2	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.	5.2 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6036 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.26 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	87.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	944.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	189.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	319.9 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	322.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	501.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	765.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	343.8 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	1229.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	327.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	310.3 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	18.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lisuride	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC	4401.0	Standard polar	33892256
Lisuride	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC	3348.7	Standard non polar	33892256
Lisuride	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@@H](CN2C)NC(=O)N(CC)CC	3447.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lisuride,1TMS,isomer #1	CCN(CC)C(=O)N[C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3056.3	Semi standard non polar	33892256
Lisuride,1TMS,isomer #1	CCN(CC)C(=O)N[C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3205.8	Standard non polar	33892256
Lisuride,1TMS,isomer #1	CCN(CC)C(=O)N[C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	4139.9	Standard polar	33892256
Lisuride,1TMS,isomer #2	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	2904.7	Semi standard non polar	33892256
Lisuride,1TMS,isomer #2	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3221.0	Standard non polar	33892256
Lisuride,1TMS,isomer #2	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3993.8	Standard polar	33892256
Lisuride,2TMS,isomer #1	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	2900.4	Semi standard non polar	33892256
Lisuride,2TMS,isomer #1	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3235.6	Standard non polar	33892256
Lisuride,2TMS,isomer #1	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3742.6	Standard polar	33892256
Lisuride,1TBDMS,isomer #1	CCN(CC)C(=O)N[C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3241.0	Semi standard non polar	33892256
Lisuride,1TBDMS,isomer #1	CCN(CC)C(=O)N[C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3420.6	Standard non polar	33892256
Lisuride,1TBDMS,isomer #1	CCN(CC)C(=O)N[C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	4209.4	Standard polar	33892256
Lisuride,1TBDMS,isomer #2	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3139.4	Semi standard non polar	33892256
Lisuride,1TBDMS,isomer #2	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3459.6	Standard non polar	33892256
Lisuride,1TBDMS,isomer #2	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	4042.8	Standard polar	33892256
Lisuride,2TBDMS,isomer #1	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3285.0	Semi standard non polar	33892256
Lisuride,2TBDMS,isomer #1	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3679.4	Standard non polar	33892256
Lisuride,2TBDMS,isomer #1	CCN(CC)C(=O)N([C@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3841.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lisuride GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-8984000000-ad76f7773ff24ccd75ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisuride GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisuride GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Lisuride 10V, Positive-QTOF	splash10-0079-2149000000-aad7057bfad12cd38426	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 20V, Positive-QTOF	splash10-00di-9372000000-fd034945ab0097bda791	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 40V, Positive-QTOF	splash10-006x-7910000000-5f786fd6b36b14de4377	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 10V, Negative-QTOF	splash10-000i-3129000000-48e9bb48d5240e0bf919	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 20V, Negative-QTOF	splash10-0079-9186000000-4db963f5c30d82e422ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 40V, Negative-QTOF	splash10-006x-9030000000-85e70fe633897c52fb45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 10V, Positive-QTOF	splash10-000i-0009000000-c19b81ddd541f33ddfb2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 20V, Positive-QTOF	splash10-0079-0098000000-14d7fc5b9b2a34896ed6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 40V, Positive-QTOF	splash10-00di-7390000000-c88b683792153c6a14eb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 10V, Negative-QTOF	splash10-000i-2209000000-3893a7ae03475c4036b4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 20V, Negative-QTOF	splash10-000i-9068000000-4ed6289e5b9a67c3bce0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisuride 40V, Negative-QTOF	splash10-0076-5291000000-03f79d302c4dd33da2c6	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 DB00589	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00589	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00589

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26847

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lisuride

METLIN ID

Not Available

PubChem Compound

28864

PDB ID

Not Available

ChEBI ID

51164

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

Not Available

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

4. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

5. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

6. 5-hydroxytryptamine receptor 2B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2B
Uniprot ID:: P41595
Molecular weight:: 54297.4

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

8. D(4) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD4
Uniprot ID:: P21917
Molecular weight:: 48359.9

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]

Enzyme Details

9. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Kimura K, Akai T, Nakamura K, Yamaguchi M, Nakagawa H, Oshino N: Dual activation by lisuride of central serotonin 5-HT(1A) and dopamine D(2) receptor sites: drug discrimination and receptor binding studies. Behav Pharmacol. 1991 Apr;2(2):105-112. [PubMed:11224054 ]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Marona-Lewicka D, Kurrasch-Orbaugh DM, Selken JR, Cumbay MG, Lisnicchia JG, Nichols DE: Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats. Psychopharmacology (Berl). 2002 Oct;164(1):93-107. Epub 2002 Jul 19. [PubMed:12373423 ]
Akai T, Takahashi M, Nakada Y, Ohnishi R, Ikoma Y, Yamaguchi M: [Anxiolytic effects of lisuride and its agonistic action to central 5-HT1A receptors]. Nihon Yakurigaku Zasshi. 1991 Apr;97(4):209-20. [PubMed:1678728 ]
Miyazawa T, Murayama C, Nakagawa H: [Effect of lisuride on experimental cerebral infarction in rats]. Nihon Yakurigaku Zasshi. 1991 Dec;98(6):449-56. [PubMed:1783326 ]
Cunningham KA, Callahan PM, Appel JB: Discriminative stimulus properties of 8-hydroxy-2-(di-n-propylamino)tetralin (8-OHDPAT): implications for understanding the actions of novel anxiolytics. Eur J Pharmacol. 1987 Jun 12;138(1):29-36. [PubMed:2887435 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
Egan CT, Herrick-Davis K, Miller K, Glennon RA, Teitler M: Agonist activity of LSD and lisuride at cloned 5HT2A and 5HT2C receptors. Psychopharmacology (Berl). 1998 Apr;136(4):409-14. [PubMed:9600588 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Showing metabocard for Lisuride (HMDB0014727)

MOL for HMDB0014727 (Lisuride)

3D MOL for HMDB0014727 (Lisuride)

3D SDF for HMDB0014727 (Lisuride)

3D-SDF for HMDB0014727 (Lisuride)

PDB for HMDB0014727 (Lisuride)

3D PDB for HMDB0014727 (Lisuride)

SMILES for HMDB0014727 (Lisuride)

INCHI for HMDB0014727 (Lisuride)

Structure for HMDB0014727 (Lisuride)

3D Structure for HMDB0014727 (Lisuride)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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