(8R)-N-[1-hydroxymethyl(propyl)]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide

Details

• Internal ID: dd685d16-6941-410d-928a-784b21528cef
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Lysergamides
• IUPAC Name: (6aR,9R)-N-(1-hydroxybutan-2-yl)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
• InChI: 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
• Popularity: 65 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₇N₃O₂
• Molecular Weight: 353.50 g/mol
• Exact Mass: 353.21032711 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 1-Methyl-D-lysergic acid butanolamide
• 1-Methylmethylergonovine
• N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
• Methysergid
• Methysergidum
• Deseril
• 1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide
• 1-Methyllysergic acid butanolamide
• Metisergide [DCIT]
• (+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide
• 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide
• Methysergidum [INN-Latin]
• Metisergido [INN-Spanish]
• Methyllysergic acid butanolamide
• (+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide
• metisergida
• N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide
• SCHEMBL467883
• CHEMBL485253
• DTXSID10859349
• BDBM50469883
• DB00247
• EN300-33419388
• (8R)-N-[1-hydroxymethyl(propyl)]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide
• (4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
• (6aR,9R)-N-(1-Hydroxy-2-butanyl)-4,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• 220756-57-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9809	98.09%
Caco-2	-	0.6778	67.78%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.4369	43.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9365	93.65%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	+	0.5975	59.75%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8816	88.16%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7148	71.48%
CYP2C9 substrate	-	0.8278	82.78%
CYP2D6 substrate	-	0.7073	70.73%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.8867	88.67%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.7910	79.10%
CYP2C8 inhibition	-	0.8061	80.61%
CYP inhibitory promiscuity	-	0.9161	91.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6213	62.13%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9973	99.73%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.9152	91.52%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7847	78.47%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8471	84.71%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7744	77.44%
Acute Oral Toxicity (c)	II	0.5768	57.68%
Estrogen receptor binding	+	0.8750	87.50%
Androgen receptor binding	+	0.7933	79.33%
Thyroid receptor binding	-	0.5236	52.36%
Glucocorticoid receptor binding	+	0.5818	58.18%
Aromatase binding	+	0.6364	63.64%
PPAR gamma	+	0.5963	59.63%
Honey bee toxicity	-	0.8905	89.05%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6433	64.33%
Fish aquatic toxicity	+	0.8186	81.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	1.585 nM; 10 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	7.586 nM	Ki	via Super-PRED
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	2.5 nM	Ki	via Super-PRED
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	79.43 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.45%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.84%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.93%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.56%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.84%	82.69%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.17%	93.56%
CHEMBL2535	P11166	Glucose transporter	90.64%	98.75%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.56%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.75%	89.00%
CHEMBL217	P14416	Dopamine D2 receptor	87.42%	95.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.71%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	85.42%	94.45%
CHEMBL5028	O14672	ADAM10	82.69%	97.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.89%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.86%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.64%	96.47%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6540428
• LOTUS: LTS0042233
• wikiData: Q105144247