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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014392

Secondary Accession Numbers

HMDB14392

Metabolite Identification

Common Name

Methysergide

Description

Methysergide, also known as metisergida, belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Methysergide is a drug which is used for the treatment of vascular headache. A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches. Methysergide is a very strong basic compound (based on its pKa). Methysergide is a potentially toxic compound.

Structure

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

  Mrv0541 04191212112D          

 27 30  0  0  0  0            999 V2000
   -3.6241    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -0.3241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4807    1.3259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1952    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    0.0884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -2.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4106   -2.3585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -0.7366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    2.5634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    0.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -3.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  2  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  2  0  0  0  0
  4 16  1  0  0  0  0
 16 15  1  0  0  0  0
 10 17  1  1  0  0  0
 11 18  1  1  0  0  0
 13 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 27  1  0  0  0  0
M  END

HMDB0014392
     RDKit          3D
Methysergide
 53 56  0  0  0  0  0  0  0  0999 V2000
    6.6423    0.8936    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.2246    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7095   -0.0274   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844   -0.9203   -0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -0.3221   -1.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070   -0.6276    0.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    0.0282   -0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    1.1158   -0.9638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.6195   -0.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1881    0.1668   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.1947   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003    1.0008   -0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1355    2.0269   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.7291   -2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5408    2.3805   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852    1.3330   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    0.6904   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.3135    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4165   -0.2850    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    0.7255   -0.2769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2131    1.1083   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0395   -1.1505    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -0.5426    1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6175   -1.4050    1.5773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.7328    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936   -0.8164    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621    1.5487    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4275    0.1152    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480    1.5315    2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6743    0.9100    1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -0.7132    1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    0.9169   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7344   -1.9171   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1129   -1.0899   -1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5668   -0.9490   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -1.5270    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099   -1.6299   -0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    0.6955   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    2.2604   -1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    3.5273   -2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    2.9055   -2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028   -0.9119    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2989    1.5902   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6183    1.7807    0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8358    0.1914   -0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -1.3882    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289   -2.1461    0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    0.2694    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431   -3.4418    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3788   -3.1286    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -2.7855   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -1.5808    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    0.1110    1.9649 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  1  0
  7  8  2  0
  7  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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26  9  1  0
 23 11  1  0
 17 12  1  0
 20 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  0
  9 37  1  6
 10 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  1
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
M  END

  Mrv0541 04191212112D          

 27 30  0  0  0  0            999 V2000
   -3.6241    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -0.3241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4807    1.3259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1952    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    0.0884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -2.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4106   -2.3585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -0.7366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    2.5634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    0.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -3.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  2  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  2  0  0  0  0
  4 16  1  0  0  0  0
 16 15  1  0  0  0  0
 10 17  1  1  0  0  0
 11 18  1  1  0  0  0
 13 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014392

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15?,19-/m1/s1

> <INCHI_KEY>
KPJZHOPZRAFDTN-NQUBZZJWSA-N

> <FORMULA>
C21H27N3O2

> <MOLECULAR_WEIGHT>
353.458

> <EXACT_MASS>
353.210327123

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.406638307352964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.816894446333333

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.999869651456585

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.00651187764884

> <JCHEM_PKA_STRONGEST_BASIC>
7.854388664235875

> <JCHEM_POLAR_SURFACE_AREA>
57.5

> <JCHEM_REFRACTIVITY>
104.4726

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methysergide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014392
     RDKit          3D
Methysergide
 53 56  0  0  0  0  0  0  0  0999 V2000
    6.6423    0.8936    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.2246    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7095   -0.0274   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844   -0.9203   -0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -0.3221   -1.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070   -0.6276    0.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    0.0282   -0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    1.1158   -0.9638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.6195   -0.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1881    0.1668   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.1947   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003    1.0008   -0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1355    2.0269   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.7291   -2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5408    2.3805   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852    1.3330   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    0.6904   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.3135    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4165   -0.2850    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    0.7255   -0.2769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2131    1.1083   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0395   -1.1505    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -0.5426    1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6175   -1.4050    1.5773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.7328    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936   -0.8164    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621    1.5487    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4275    0.1152    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480    1.5315    2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6743    0.9100    1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -0.7132    1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    0.9169   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7344   -1.9171   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1129   -1.0899   -1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5668   -0.9490   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -1.5270    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099   -1.6299   -0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    0.6955   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    2.2604   -1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    3.5273   -2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    2.9055   -2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028   -0.9119    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2989    1.5902   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6183    1.7807    0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8358    0.1914   -0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -1.3882    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289   -2.1461    0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    0.2694    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431   -3.4418    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3788   -3.1286    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -2.7855   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -1.5808    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    0.1110    1.9649 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  1  0
  7  8  2  0
  7  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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26  9  1  0
 23 11  1  0
 17 12  1  0
 20 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  0
  9 37  1  6
 10 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  1
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -6.765   0.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.099  -0.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.099  -2.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.765  -2.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.431  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.431  -0.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.098   0.165   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.098  -2.915   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.764  -2.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.764  -0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.764   2.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.098   1.705   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.430   0.165   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.430   1.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.496  -4.403   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -6.366  -4.403   0.000  0.00  0.00           N+0
HETATM   17  H   UNK     0      -1.430  -1.375   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      -2.764   4.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.097  -0.605   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -1.430   4.785   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -0.097   4.015   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.237   4.785   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.571   4.015   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.098   4.785   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.097   2.475   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.237   1.705   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -7.136  -5.736   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10   12                                                  
CONECT    8    5    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   13    7   17                                             
CONECT   11   12   14   18                                                  
CONECT   12    7   11                                                       
CONECT   13   10   14   19                                                  
CONECT   14   11   13                                                       
CONECT   15    8   16                                                       
CONECT   16    4   15   27                                                  
CONECT   17   10                                                            
CONECT   18   11   20   24                                                  
CONECT   19   13                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   21   26                                                       
CONECT   26   25                                                            
CONECT   27   16                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0014392
HETATM    1  C1  UNL     1       6.642   0.894   1.096  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.312   0.225   1.268  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.710  -0.027  -0.098  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.584  -0.920  -0.935  1.00  0.00           C  
HETATM    5  O1  UNL     1       6.810  -0.322  -1.152  1.00  0.00           O  
HETATM    6  N1  UNL     1       3.407  -0.628   0.138  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.248   0.028  -0.342  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.341   1.116  -0.964  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.938  -0.620  -0.079  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.188   0.167  -0.631  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.337   0.195  -0.055  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.400   1.001  -0.670  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.135   2.027  -1.534  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.232   2.729  -2.065  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.541   2.380  -1.714  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.785   1.333  -0.833  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.685   0.690  -0.352  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.042  -0.314   0.500  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.417  -0.285   0.542  1.00  0.00           C  
HETATM   20  N2  UNL     1      -5.848   0.726  -0.277  1.00  0.00           N  
HETATM   21  C17 UNL     1      -7.213   1.108  -0.530  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.039  -1.151   1.149  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.672  -0.543   1.201  1.00  0.00           C  
HETATM   24  N3  UNL     1      -0.617  -1.405   1.577  1.00  0.00           N  
HETATM   25  C20 UNL     1      -0.676  -2.733   1.071  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.694  -0.816   1.395  1.00  0.00           C  
HETATM   27  H1  UNL     1       6.662   1.549   0.198  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.427   0.115   1.034  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.848   1.531   2.010  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.674   0.910   1.859  1.00  0.00           H  
HETATM   31  H5  UNL     1       5.386  -0.713   1.850  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.566   0.917  -0.656  1.00  0.00           H  
HETATM   33  H7  UNL     1       5.734  -1.917  -0.457  1.00  0.00           H  
HETATM   34  H8  UNL     1       5.113  -1.090  -1.922  1.00  0.00           H  
HETATM   35  H9  UNL     1       7.567  -0.949  -1.193  1.00  0.00           H  
HETATM   36  H10 UNL     1       3.382  -1.527   0.656  1.00  0.00           H  
HETATM   37  H11 UNL     1       1.010  -1.630  -0.568  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.064   0.695  -1.548  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.135   2.260  -1.770  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.037   3.527  -2.736  1.00  0.00           H  
HETATM   41  H15 UNL     1      -5.399   2.905  -2.109  1.00  0.00           H  
HETATM   42  H16 UNL     1      -6.103  -0.912   1.096  1.00  0.00           H  
HETATM   43  H17 UNL     1      -7.299   1.590  -1.524  1.00  0.00           H  
HETATM   44  H18 UNL     1      -7.618   1.781   0.262  1.00  0.00           H  
HETATM   45  H19 UNL     1      -7.836   0.191  -0.542  1.00  0.00           H  
HETATM   46  H20 UNL     1      -3.402  -1.388   2.171  1.00  0.00           H  
HETATM   47  H21 UNL     1      -3.029  -2.146   0.615  1.00  0.00           H  
HETATM   48  H22 UNL     1      -1.729   0.269   1.990  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.243  -3.442   1.705  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.379  -3.129   1.054  1.00  0.00           H  
HETATM   51  H25 UNL     1      -1.006  -2.785  -0.000  1.00  0.00           H  
HETATM   52  H26 UNL     1       1.431  -1.581   1.744  1.00  0.00           H  
HETATM   53  H27 UNL     1       0.735   0.111   1.965  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4    6   32
CONECT    4    5   33   34
CONECT    5   35
CONECT    6    7   36
CONECT    7    8    8    9
CONECT    9   10   26   37
CONECT   10   11   11   38
CONECT   11   12   23
CONECT   12   13   13   17
CONECT   13   14   39
CONECT   14   15   15   40
CONECT   15   16   41
CONECT   16   17   17   20
CONECT   17   18
CONECT   18   19   19   22
CONECT   19   20   42
CONECT   20   21
CONECT   21   43   44   45
CONECT   22   23   46   47
CONECT   23   24   48
CONECT   24   25   26
CONECT   25   49   50   51
CONECT   26   52   53
END

HMDB0014392
     RDKit          3D
Methysergide
 53 56  0  0  0  0  0  0  0  0999 V2000
    6.6423    0.8936    1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.2246    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7095   -0.0274   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844   -0.9203   -0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -0.3221   -1.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070   -0.6276    0.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    0.0282   -0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    1.1158   -0.9638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.6195   -0.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1881    0.1668   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.1947   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003    1.0008   -0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1355    2.0269   -1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319    2.7291   -2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5408    2.3805   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852    1.3330   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    0.6904   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.3135    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4165   -0.2850    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    0.7255   -0.2769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2131    1.1083   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0395   -1.1505    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -0.5426    1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6175   -1.4050    1.5773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.7328    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936   -0.8164    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621    1.5487    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4275    0.1152    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480    1.5315    2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6743    0.9100    1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -0.7132    1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    0.9169   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7344   -1.9171   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1129   -1.0899   -1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5668   -0.9490   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -1.5270    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099   -1.6299   -0.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644    0.6955   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    2.2604   -1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    3.5273   -2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    2.9055   -2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028   -0.9119    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2989    1.5902   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6183    1.7807    0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8358    0.1914   -0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -1.3882    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289   -2.1461    0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    0.2694    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2431   -3.4418    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3788   -3.1286    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -2.7855   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -1.5808    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    0.1110    1.9649 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  1  0
  7  8  2  0
  7  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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26  9  1  0
 23 11  1  0
 17 12  1  0
 20 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  0
  9 37  1  6
 10 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  1
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide	ChEBI
(+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide	ChEBI
1-Methyl-D-lysergic acid butanolamide	ChEBI
1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide	ChEBI
1-Methyllysergic acid butanolamide	ChEBI
1-Methylmethylergonovine	ChEBI
9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide	ChEBI
Methysergidum	ChEBI
Metisergida	ChEBI
N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide	ChEBI
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8b-carboxamide	Generator
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8β-carboxamide	Generator
1-Methyl-D-lysergate butanolamide	Generator
1-Methyl-dextro-lysergate (+)-1-hydroxy-2-butylamide	Generator
1-Methyllysergate butanolamide	Generator
Methyllysergic acid butanolamide	HMDB
Methysergid	HMDB
Metisergide	HMDB
N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide	HMDB
1-Methyllysergic acid butanolamide tartrate, (R-(r,r))-(8beta)-isomer	HMDB

Chemical Formula

C₂₁H₂₇N₃O₂

Average Molecular Weight

353.458

Monoisotopic Molecular Weight

353.210327123

IUPAC Name

(4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

Traditional Name

methysergide

CAS Registry Number

361-37-5

SMILES

[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO

InChI Identifier

InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15?,19-/m1/s1

InChI Key

KPJZHOPZRAFDTN-NQUBZZJWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Lysergamides

Alternative Parents

Substituents

Lysergic acid amide
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline-3-carboxamide
N-alkylindole
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
N-methylpyrrole
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Carboxamide group
Amino acid or derivatives
Tertiary amine
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:584020 )
ergot alkaloid (CHEBI:584020 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0014392)

Process

Not Available

Role

Industrial application

Vasoconstrictor agent (HMDB: HMDB0014392)
Serotonergic antagonist (HMDB: HMDB0014392)
Sympatholytic agent (HMDB: HMDB0014392)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.22 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.82	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.47 m³·mol⁻¹	ChemAxon
Polarizability	40.41 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]+	182.811	31661259
DarkChem	[M-H]-	178.375	31661259
DeepCCS	[M-2H]-	222.183	30932474
DeepCCS	[M+Na]+	197.208	30932474
AllCCS	[M+H]+	187.9	32859911
AllCCS	[M+H-H2O]+	185.1	32859911
AllCCS	[M+NH4]+	190.4	32859911
AllCCS	[M+Na]+	191.1	32859911
AllCCS	[M-H]-	189.3	32859911
AllCCS	[M+Na-2H]-	189.6	32859911
AllCCS	[M+HCOO]-	190.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methysergide	[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO	4495.9	Standard polar	33892256
Methysergide	[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO	3096.7	Standard non polar	33892256
Methysergide	[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO	3369.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methysergide,1TMS,isomer #1	CCC(CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1	2997.8	Semi standard non polar	33892256
Methysergide,1TMS,isomer #2	CCC(CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C	2995.0	Semi standard non polar	33892256
Methysergide,2TMS,isomer #1	CCC(CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C	2977.9	Semi standard non polar	33892256
Methysergide,2TMS,isomer #1	CCC(CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C	3212.2	Standard non polar	33892256
Methysergide,2TMS,isomer #1	CCC(CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C	3870.0	Standard polar	33892256
Methysergide,1TBDMS,isomer #1	CCC(CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1	3239.4	Semi standard non polar	33892256
Methysergide,1TBDMS,isomer #2	CCC(CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3206.4	Semi standard non polar	33892256
Methysergide,2TBDMS,isomer #1	CCC(CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3385.3	Semi standard non polar	33892256
Methysergide,2TBDMS,isomer #1	CCC(CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3680.4	Standard non polar	33892256
Methysergide,2TBDMS,isomer #1	CCC(CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3982.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methysergide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-4495000000-d0cc0e065ac2a249f139	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methysergide GC-MS (1 TMS) - 70eV, Positive	splash10-03di-3390100000-c2e2183c67e221dc8c1d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methysergide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methysergide 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 - Methysergide 10V, Positive-QTOF	splash10-0udr-1009000000-633c43ec26d6039658e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 20V, Positive-QTOF	splash10-00kr-5095000000-47b5108f6a3ebd949236	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 40V, Positive-QTOF	splash10-0c0c-3390000000-7d1562a443e084f1ea99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 10V, Negative-QTOF	splash10-0udi-0009000000-9ba72bc3d8d89f6a4388	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 20V, Negative-QTOF	splash10-0ff9-2059000000-819b11151769bcbb6445	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 40V, Negative-QTOF	splash10-05g3-6090000000-5d7ac6f788f61ce26929	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 10V, Positive-QTOF	splash10-0udi-0019000000-5a70e47475b13679f8e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 20V, Positive-QTOF	splash10-0udr-0059000000-d42a975e818a2288348e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 40V, Positive-QTOF	splash10-000i-0090000000-22d20459936ae0d0b518	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 10V, Negative-QTOF	splash10-0udi-0009000000-c66b7fea4f08e0ca5b51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 20V, Negative-QTOF	splash10-0udi-1019000000-b7eebee23bde51802f58	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysergide 40V, Negative-QTOF	splash10-0kfx-6193000000-c592c6e25521a17d4740	2021-09-22	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 DB00247	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00247	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

DB00247

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5022813

KEGG Compound ID

C07199

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methysergide

METLIN ID

Not Available

PubChem Compound

6540428

PDB ID

Not Available

ChEBI ID

584020

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

Enzymes

Enzyme Details

1. 5-hydroxytryptamine receptor 7

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 stimulate adenylate cyclase
Gene Name:: HTR7
Uniprot ID:: P34969
Molecular weight:: 53554.4

References

Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]

Enzyme Details

2. 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

Schmuck K, Ullmer C, Kalkman HO, Probst A, Lubbert H: Activation of meningeal 5-HT2B receptors: an early step in the generation of migraine headache? Eur J Neurosci. 1996 May;8(5):959-67. [PubMed:8743744 ]

Enzyme Details

3. 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

Scrogin KE, Johnson AK, Brooks VL: Methysergide delays the decompensatory responses to severe hemorrhage by activating 5-HT(1A) receptors. Am J Physiol Regul Integr Comp Physiol. 2000 Nov;279(5):R1776-86. [PubMed:11049861 ]
Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]
Sugimoto Y, Inoue K, Yamada J: Involvement of 5-HT(2) receptor in imipramine-induced hyperglycemia in mice. Horm Metab Res. 2003 Sep;35(9):511-6. [PubMed:14517765 ]
Skyba DA, Radhakrishnan R, Rohlwing JJ, Wright A, Sluka KA: Joint manipulation reduces hyperalgesia by activation of monoamine receptors but not opioid or GABA receptors in the spinal cord. Pain. 2003 Nov;106(1-2):159-68. [PubMed:14581123 ]
Pranzatelli MR, Balletti J: Characterization of 5-hydroxytryptamine 1A-like binding sites in human ganglioneuroblastoma. Neurosci Lett. 1991 Oct 28;132(1):117-20. [PubMed:1838579 ]

Enzyme Details

4. 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

Castilho VM, Avanzi V, Brandao ML: Antinociception elicited by aversive stimulation of the inferior colliculus. Pharmacol Biochem Behav. 1999 Mar;62(3):425-31. [PubMed:10080233 ]
Geerts IS, Matthys KE, Herman AG, Bult H: Involvement of 5-HT1B receptors in collar-induced hypersensitivity to 5-hydroxytryptamine of the rabbit carotid artery. Br J Pharmacol. 1999 Jul;127(6):1327-36. [PubMed:10455282 ]
Shaw AM, Brown C, Irvine J, Bunton DC, MacDonald A: Role of the 5-HT(2A)receptor and alpha(1)-adrenoceptor in the contractile response of rat pulmonary artery to 5-HT in the presence and absence of nitric oxide. Pulm Pharmacol Ther. 2000;13(6):277-85. [PubMed:11061982 ]
Prins NH, Akkermans LM, Lefebvre RA, Schuurkes JA: Characterization of the receptors involved in the 5-HT-induced excitation of canine antral longitudinal muscle. Br J Pharmacol. 2001 Nov;134(6):1351-9. [PubMed:11704657 ]
Connor JD, Rasheed H, Gilani AH, Cheema M, Rizvi Z, Saeed SA: Second messengers in platelet aggregation evoked by serotonin and A23187, a calcium ionophore. Life Sci. 2001 Oct 26;69(23):2759-64. [PubMed:11720080 ]

Enzyme Details

5. 5-hydroxytryptamine receptor 2C

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:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Johnson MP, Lea RA, Curtain RP, MacMillan JC, Griffiths LR: An investigation of the 5-HT2C receptor gene as a migraine candidate gene. Am J Med Genet B Neuropsychiatr Genet. 2003 Feb;117B(1):86-9. [PubMed:12555241 ]

Showing metabocard for Methysergide (HMDB0014392)

MOL for HMDB0014392 (Methysergide)

3D MOL for HMDB0014392 (Methysergide)

3D SDF for HMDB0014392 (Methysergide)

3D-SDF for HMDB0014392 (Methysergide)

PDB for HMDB0014392 (Methysergide)

3D PDB for HMDB0014392 (Methysergide)

SMILES for HMDB0014392 (Methysergide)

INCHI for HMDB0014392 (Methysergide)

Structure for HMDB0014392 (Methysergide)

3D Structure for HMDB0014392 (Methysergide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References