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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014497

Secondary Accession Numbers

HMDB14497

Metabolite Identification

Common Name

Methylergonovine

Description

Methylergonovine, also known as ergotyl or methylergobasin, belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Its specific binding and activation pattern on these receptors leads to a highly, if not completely, specific contraction of smooth uterus muscle via 5-HT2A serotonin receptors, while blood vessels are affected to a lesser extent compared to other ergot alkaloids. Due to its oxytocic properties, it has a medical use in obstetrics. It is available as tablets or injection (IM or IV) or in liquid form to be taken orally. Methylergonovine is a drug which is used for the prevention and control of excessive bleeding following vaginal childbirth. It is also contraindicated in HIV positive patients taking protease inhibitors, delavirdine and efavirenz (which is also an agonist at the 5HT2A-mGlu2 receptor protomer and increases the chances of a patient experiencing hallucinations during methylergometrine therapy). Methylergometrine (also called methylergonovine, methylergobasin, and D-lysergic acid 1-butanolamide) is a synthetic analogue of ergometrine, a psychedelic alkaloid found in ergot, and many species of morning glory. Methylergonovine is a very strong basic compound (based on its pKa). Methylergonovine is a potentially toxic compound. It can also increase constriction of blood vessels caused by sympathomimetic drugs and other ergot alkaloids. Methylergometrine likely interacts with drugs that inhibit the liver enzyme CYP3A4, such as azole antifungals, macrolide antibiotics and many HIV drugs. Methylergometrine maleate is marketed under the trade name Methergine.

Structure

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

8226
  Mrv0541 02231214372D          

 26 29  0  0  1  0            999 V2000
    3.0853    0.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3596    3.1421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993    0.2572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8144   -3.1997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    1.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860   -0.6021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2715   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7005   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    0.2628    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2584    0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7005   -1.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715   -1.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860   -2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993   -3.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7184    0.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981    0.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2103   -2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2584   -3.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142   -3.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.9073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3661    1.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0757    2.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5960   -0.2562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
  2 24  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  4 18  1  0  0  0  0
  5 17  1  0  0  0  0
 22  5  1  1  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
  9 17  1  1  0  0  0
 11 13  1  0  0  0  0
 11 18  2  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

HMDB0014497
     RDKit          3D
Methylergonovine
 50 53  0  0  0  0  0  0  0  0999 V2000
   -6.5331   -0.1190    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2423   -0.1313    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1002   -0.0606   -0.1358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1693    1.2013   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333    2.3496   -0.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -0.0692    0.5116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8849   -1.0901    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044   -1.9467   -0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412   -1.1792    0.7616 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2548    0.0660    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.0017    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247    1.2658   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020    2.4528   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    3.5692   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862    3.4873   -0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046    2.2981   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    1.8474   -0.0539 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447    0.5127    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    0.0796    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978    1.1960   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381   -1.1942    0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2638   -1.2642   -0.0484 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5571   -2.3204    0.6456 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276   -3.6256    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -2.3305    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9383    0.8866   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2541   -0.7865    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3170   -0.6542   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -1.0929    1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2498    0.7244    1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434   -0.9043   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    1.2014   -1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    1.2482   -1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.5289    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5434    0.6525    1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -1.3346    1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258    1.0451    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290    2.5037   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    4.5361   -0.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    4.3537   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5065    2.4541   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828   -0.1406    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -2.0588    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -1.3424    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -1.4743   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1513   -3.7223   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1050   -3.7702    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798   -4.3715    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -2.2206   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3383   -3.2548    0.3874 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  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
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  9 36  1  1
 10 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  6
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

8226
  Mrv0541 02231214372D          

 26 29  0  0  1  0            999 V2000
    3.0853    0.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3596    3.1421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993    0.2572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8144   -3.1997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950    1.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860   -0.6021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2715   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7005   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    0.2628    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2584    0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7005   -1.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715   -1.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9860   -2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993   -3.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7184    0.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981    0.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2103   -2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2584   -3.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142   -3.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.9073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3661    1.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0757    2.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5960   -0.2562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
  2 24  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  4 18  1  0  0  0  0
  5 17  1  0  0  0  0
 22  5  1  1  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
  9 17  1  1  0  0  0
 11 13  1  0  0  0  0
 11 18  2  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014497

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1

> <INCHI_KEY>
UNBRKDKAWYKMIV-QWQRMKEZSA-N

> <FORMULA>
C20H25N3O2

> <MOLECULAR_WEIGHT>
339.4314

> <EXACT_MASS>
339.194677059

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.72984221073561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.5932183806666667

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.94889202988126

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.997192550970546

> <JCHEM_PKA_STRONGEST_BASIC>
7.927308778613017

> <JCHEM_POLAR_SURFACE_AREA>
68.36

> <JCHEM_REFRACTIVITY>
99.5759

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylergonovine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014497
     RDKit          3D
Methylergonovine
 50 53  0  0  0  0  0  0  0  0999 V2000
   -6.5331   -0.1190    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2423   -0.1313    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1002   -0.0606   -0.1358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1693    1.2013   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333    2.3496   -0.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -0.0692    0.5116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8849   -1.0901    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044   -1.9467   -0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412   -1.1792    0.7616 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2548    0.0660    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.0017    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247    1.2658   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020    2.4528   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    3.5692   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862    3.4873   -0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046    2.2981   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    1.8474   -0.0539 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447    0.5127    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    0.0796    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978    1.1960   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381   -1.1942    0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2638   -1.2642   -0.0484 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5571   -2.3204    0.6456 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276   -3.6256    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -2.3305    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9383    0.8866   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2541   -0.7865    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3170   -0.6542   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -1.0929    1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2498    0.7244    1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434   -0.9043   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    1.2014   -1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    1.2482   -1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.5289    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5434    0.6525    1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -1.3346    1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258    1.0451    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290    2.5037   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    4.5361   -0.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    4.3537   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5065    2.4541   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828   -0.1406    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -2.0588    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -1.3424    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -1.4743   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1513   -3.7223   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1050   -3.7702    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798   -4.3715    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -2.2206   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3383   -3.2548    0.3874 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  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
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  9 36  1  1
 10 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  6
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 8226                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.759   0.480   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.405   5.865   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      11.199   0.480   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      12.720  -5.973   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.084   2.796   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.174  -1.124   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.840  -1.894   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.508  -1.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.427   0.491   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.816   1.293   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.508  -3.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.840  -3.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.174  -4.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.439  -1.113   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.199  -5.808   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.541   1.234   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.090   1.256   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.459  -4.633   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.439  -4.215   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.816  -6.621   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.427  -5.819   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.747   3.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.417   2.785   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.741   5.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   3.550   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      12.313  -0.478   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   24                                                            
CONECT    3    6   10   16                                                  
CONECT    4   15   18                                                       
CONECT    5   17   22                                                       
CONECT    6    3    7    8   26                                             
CONECT    7    6   12   14                                                  
CONECT    8    6   11                                                       
CONECT    9   10   14   17                                                  
CONECT   10    3    9                                                       
CONECT   11    8   13   18                                                  
CONECT   12    7   13   19                                                  
CONECT   13   11   12   15                                                  
CONECT   14    7    9                                                       
CONECT   15    4   13   20                                                  
CONECT   16    3                                                            
CONECT   17    1    5    9                                                  
CONECT   18    4   11                                                       
CONECT   19   12   21                                                       
CONECT   20   15   21                                                       
CONECT   21   19   20                                                       
CONECT   22    5   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24    2   22                                                       
CONECT   25   23                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0014497
HETATM    1  C1  UNL     1      -6.533  -0.119   0.041  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.242  -0.131   0.853  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.100  -0.061  -0.136  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.169   1.201  -0.972  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.033   2.350  -0.201  1.00  0.00           O  
HETATM    6  N1  UNL     1      -2.815  -0.069   0.512  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.885  -1.090   0.150  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.204  -1.947  -0.712  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.541  -1.179   0.762  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.255   0.066   0.506  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.495  -0.002   0.146  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.225   1.266  -0.091  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.602   2.453  -0.384  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.391   3.569  -0.592  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.786   3.487  -0.506  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.405   2.298  -0.214  1.00  0.00           C  
HETATM   17  N2  UNL     1       5.665   1.847  -0.054  1.00  0.00           N  
HETATM   18  C14 UNL     1       5.645   0.513   0.239  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.324   0.080   0.272  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.598   1.196  -0.009  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.638  -1.194   0.523  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.264  -1.264  -0.048  1.00  0.00           C  
HETATM   23  N3  UNL     1       1.557  -2.320   0.646  1.00  0.00           N  
HETATM   24  C19 UNL     1       2.128  -3.626   0.362  1.00  0.00           C  
HETATM   25  C20 UNL     1       0.197  -2.331   0.139  1.00  0.00           C  
HETATM   26  H1  UNL     1      -6.938   0.887  -0.099  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.254  -0.786   0.596  1.00  0.00           H  
HETATM   28  H3  UNL     1      -6.317  -0.654  -0.904  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.168  -1.093   1.398  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.250   0.724   1.536  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.143  -0.904  -0.847  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.400   1.201  -1.769  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.161   1.248  -1.510  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.107   2.529   0.046  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.543   0.652   1.240  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.569  -1.335   1.855  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.226   1.045   0.631  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.529   2.504  -0.451  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.966   4.536  -0.826  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.418   4.354  -0.667  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.507   2.454  -0.147  1.00  0.00           H  
HETATM   42  H17 UNL     1       6.483  -0.141   0.423  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.217  -2.059   0.104  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.536  -1.342   1.638  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.308  -1.474  -1.154  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.151  -3.722  -0.742  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.105  -3.770   0.832  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.380  -4.372   0.724  1.00  0.00           H  
HETATM   49  H24 UNL     1       0.166  -2.221  -0.964  1.00  0.00           H  
HETATM   50  H25 UNL     1      -0.338  -3.255   0.387  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    6   31
CONECT    4    5   32   33
CONECT    5   34
CONECT    6    7   35
CONECT    7    8    8    9
CONECT    9   10   25   36
CONECT   10   11   11   37
CONECT   11   12   22
CONECT   12   13   13   20
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   40
CONECT   16   17   20   20
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   21
CONECT   21   22   43   44
CONECT   22   23   45
CONECT   23   24   25
CONECT   24   46   47   48
CONECT   25   49   50
END

HMDB0014497
     RDKit          3D
Methylergonovine
 50 53  0  0  0  0  0  0  0  0999 V2000
   -6.5331   -0.1190    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2423   -0.1313    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1002   -0.0606   -0.1358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1693    1.2013   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333    2.3496   -0.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -0.0692    0.5116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8849   -1.0901    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044   -1.9467   -0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412   -1.1792    0.7616 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2548    0.0660    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.0017    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247    1.2658   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020    2.4528   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    3.5692   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862    3.4873   -0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046    2.2981   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    1.8474   -0.0539 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6447    0.5127    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    0.0796    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978    1.1960   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381   -1.1942    0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2638   -1.2642   -0.0484 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5571   -2.3204    0.6456 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276   -3.6256    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -2.3305    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9383    0.8866   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2541   -0.7865    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3170   -0.6542   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -1.0929    1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2498    0.7244    1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434   -0.9043   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    1.2014   -1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606    1.2482   -1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.5289    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5434    0.6525    1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -1.3346    1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258    1.0451    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290    2.5037   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    4.5361   -0.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    4.3537   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5065    2.4541   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828   -0.1406    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -2.0588    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -1.3424    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -1.4743   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1513   -3.7223   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1050   -3.7702    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798   -4.3715    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -2.2206   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3383   -3.2548    0.3874 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  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
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  9 36  1  1
 10 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  6
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ergotyl	Kegg
Methylergobasin	HMDB
Methylergobasine	HMDB
Methylergobrevin	HMDB
Methylergometrin	HMDB
Methylergometrine	HMDB
Methylergonovin	HMDB
Methylergonovine maleate	HMDB
Novartis brand OF methylergonovine maleate	HMDB
Méthergin	HMDB
Methergin	HMDB
Methergine	HMDB
Methylergometrine maleate	HMDB
Methylergonovine	MeSH

Chemical Formula

C₂₀H₂₅N₃O₂

Average Molecular Weight

339.4314

Monoisotopic Molecular Weight

339.194677059

IUPAC Name

(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

methylergonovine

CAS Registry Number

113-42-8

SMILES

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

InChI Identifier

InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1

InChI Key

UNBRKDKAWYKMIV-QWQRMKEZSA-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
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Primary alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location

Non-excretory biofluid

Blood

Excreta

Urine

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.2 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	7.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.58 m³·mol⁻¹	ChemAxon
Polarizability	38.73 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]+	180.081	31661259
DarkChem	[M-H]-	177.974	31661259
DeepCCS	[M-2H]-	217.158	30932474
DeepCCS	[M+Na]+	192.199	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylergonovine	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO	4696.4	Standard polar	33892256
Methylergonovine	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO	3426.4	Standard non polar	33892256
Methylergonovine	[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO	3503.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylergonovine,1TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1	3071.4	Semi standard non polar	33892256
Methylergonovine,1TMS,isomer #2	CC[C@@H](CO)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3088.2	Semi standard non polar	33892256
Methylergonovine,1TMS,isomer #3	CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3020.8	Semi standard non polar	33892256
Methylergonovine,2TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3039.4	Semi standard non polar	33892256
Methylergonovine,2TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	3286.9	Standard non polar	33892256
Methylergonovine,2TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C	4010.4	Standard polar	33892256
Methylergonovine,2TMS,isomer #2	CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3016.9	Semi standard non polar	33892256
Methylergonovine,2TMS,isomer #2	CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3243.2	Standard non polar	33892256
Methylergonovine,2TMS,isomer #2	CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1	3951.0	Standard polar	33892256
Methylergonovine,2TMS,isomer #3	CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	2995.8	Semi standard non polar	33892256
Methylergonovine,2TMS,isomer #3	CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3245.0	Standard non polar	33892256
Methylergonovine,2TMS,isomer #3	CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	4002.6	Standard polar	33892256
Methylergonovine,3TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3036.6	Semi standard non polar	33892256
Methylergonovine,3TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3272.9	Standard non polar	33892256
Methylergonovine,3TMS,isomer #1	CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C	3762.7	Standard polar	33892256
Methylergonovine,1TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1	3303.9	Semi standard non polar	33892256
Methylergonovine,1TBDMS,isomer #2	CC[C@@H](CO)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3290.6	Semi standard non polar	33892256
Methylergonovine,1TBDMS,isomer #3	CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3251.7	Semi standard non polar	33892256
Methylergonovine,2TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3460.5	Semi standard non polar	33892256
Methylergonovine,2TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	3753.4	Standard non polar	33892256
Methylergonovine,2TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C	4096.3	Standard polar	33892256
Methylergonovine,2TBDMS,isomer #2	CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3432.3	Semi standard non polar	33892256
Methylergonovine,2TBDMS,isomer #2	CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	3672.9	Standard non polar	33892256
Methylergonovine,2TBDMS,isomer #2	CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1	4060.2	Standard polar	33892256
Methylergonovine,2TBDMS,isomer #3	CC[C@@H](CO)N(C(=O)[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	3407.6	Semi standard non polar	33892256
Methylergonovine,2TBDMS,isomer #3	CC[C@@H](CO)N(C(=O)[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	3700.6	Standard non polar	33892256
Methylergonovine,2TBDMS,isomer #3	CC[C@@H](CO)N(C(=O)[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	4078.6	Standard polar	33892256
Methylergonovine,3TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[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	3610.0	Semi standard non polar	33892256
Methylergonovine,3TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[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	3915.1	Standard non polar	33892256
Methylergonovine,3TBDMS,isomer #1	CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[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	3914.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylergonovine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3914000000-d6349f005e3253821421	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylergonovine GC-MS (1 TMS) - 70eV, Positive	splash10-01ba-4095000000-07cac91c483c45e0b4fc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylergonovine 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 - Methylergonovine 10V, Positive-QTOF	splash10-006x-1019000000-5743eb114639a8b4cd68	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 20V, Positive-QTOF	splash10-0uk9-4093000000-2f215482a3bef9973b4f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 40V, Positive-QTOF	splash10-00di-3940000000-bf7ef321bb426974d49b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 10V, Negative-QTOF	splash10-000i-0019000000-25ad156f1bdbadfdb37f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 20V, Negative-QTOF	splash10-05g0-2169000000-04eae81fd7d7bb4dbf72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 40V, Negative-QTOF	splash10-05fu-8290000000-0f17abb269c859d8cdac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 10V, Positive-QTOF	splash10-0006-0019000000-011f8e74477076271412	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 20V, Positive-QTOF	splash10-006x-1069000000-38039c479f71c2219d4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 40V, Positive-QTOF	splash10-00di-0190000000-68a0ea065cbe0f2aeef0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 10V, Negative-QTOF	splash10-000i-0009000000-7d83f1b1716bd17dabc8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 20V, Negative-QTOF	splash10-000i-0009000000-4856ff7ce1f702c342f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylergonovine 40V, Negative-QTOF	splash10-0avl-5290000000-bb401d09f7282c1260d2	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 DB00353	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00353	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

DB00353

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7933

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylergometrine

METLIN ID

Not Available

PubChem Compound

8226

PDB ID

Not Available

ChEBI ID

775307

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. 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

Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [PubMed:12583687 ]

Enzyme Details

2. D(1A) 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 activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Reyes FD, Mozzachiodi R, Baxter DA, Byrne JH: Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20. [PubMed:15930499 ]
Nargeot R, Baxter DA, Patterson GW, Byrne JH: Dopaminergic synapses mediate neuronal changes in an analogue of operant conditioning. J Neurophysiol. 1999 Apr;81(4):1983-7. [PubMed:10200235 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Methylergonovine (HMDB0014497)

MOL for HMDB0014497 (Methylergonovine)

3D MOL for HMDB0014497 (Methylergonovine)

3D SDF for HMDB0014497 (Methylergonovine)

3D-SDF for HMDB0014497 (Methylergonovine)

PDB for HMDB0014497 (Methylergonovine)

3D PDB for HMDB0014497 (Methylergonovine)

SMILES for HMDB0014497 (Methylergonovine)

INCHI for HMDB0014497 (Methylergonovine)

Structure for HMDB0014497 (Methylergonovine)

3D Structure for HMDB0014497 (Methylergonovine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References