Ergometrinine

Details

• Internal ID: 8090ce44-4d04-4eca-bdfd-2e8839a7d609
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Lysergamides
• IUPAC Name: (6aR,9S)-N-[(2S)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• SMILES (Canonical): CC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
• SMILES (Isomeric): C[C@@H](CO)NC(=O)[C@@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
• InChI: InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13-,17+/m0/s1
• InChI Key: WVVSZNPYNCNODU-PLQHRBFRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₃N₃O₂
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.17902698 g/mol
• Topological Polar Surface Area (TPSA): 68.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Ergometrinin
• Ergonovinine
• Ergobasinine
• Isoergometrine
• Ergobasinin
• 479-00-5
• 5EXN22NGMW
• (6aR,9S)-N-[(2S)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• UNII-5EXN22NGMW
• BRN 0094900
• D-lysergic acid D-propanolamide
• Ergonovinine;Ergobasinine
• ERGOMETRININE [MI]
• 9,10-Didehydro-N-((S)-2-hydroxy-1-methylethyl)-6-methylergoline-8-alpha-carboxamide
• 4-25-00-00950 (Beilstein Handbook Reference)
• SCHEMBL918411
• CHEMBL1555758
• DTXSID90893241
• TNP00144
• Ergometrinine dried down 25 microg/mL
• Ergoline-8-alpha-carboxamide, 9,10-didehydro-N-((S)-2-hydroxy-1-methylethyl)-6-methyl-
• NCGC00017253-01
• ERGOMETRINE MALEATE IMPURITY F [EP IMPURITY]
• Q15633935
• (8alpha)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide
• (6aR,9S)-N-[(S)-1-hydroxypropan-2-yl]-7-methyl- 4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• (8.ALPHA.)-9,10-DIDEHYDRO-N-((1S)-2-HYDROXY-1-METHYLETHYL)-6-METHYLERGOLINE-8-CARBOXAMIDE
• ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N-((1S)-2-HYDROXY-1-METHYLETHYL)-6-METHYL-, (8.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9717	97.17%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.5333	53.33%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9384	93.84%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	+	0.6098	60.98%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7878	78.78%
P-glycoprotein inhibitior	-	0.9388	93.88%
P-glycoprotein substrate	+	0.8258	82.58%
CYP3A4 substrate	+	0.7979	79.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6884	68.84%
CYP3A4 inhibition	-	0.9228	92.28%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.7284	72.84%
CYP2C8 inhibition	-	0.8798	87.98%
CYP inhibitory promiscuity	-	0.9236	92.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6595	65.95%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9990	99.90%
Skin irritation	-	0.7620	76.20%
Skin corrosion	-	0.9197	91.97%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8404	84.04%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.8589	85.89%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	II	0.6619	66.19%
Estrogen receptor binding	+	0.6184	61.84%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	-	0.8320	83.20%
Glucocorticoid receptor binding	-	0.5961	59.61%
Aromatase binding	-	0.5528	55.28%
PPAR gamma	-	0.5697	56.97%
Honey bee toxicity	-	0.8877	88.77%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.7927	79.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	398.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.34%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.95%	96.09%
CHEMBL2094135	Q96BI3	Gamma-secretase	95.68%	98.05%
CHEMBL4040	P28482	MAP kinase ERK2	94.54%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.39%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.43%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.12%	82.69%
CHEMBL2535	P11166	Glucose transporter	90.79%	98.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.41%	93.03%
CHEMBL217	P14416	Dopamine D2 receptor	88.27%	95.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.96%	93.56%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.88%	83.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.18%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.54%	88.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.47%	96.47%
CHEMBL4073	P09237	Matrix metalloproteinase 7	84.25%	97.56%
CHEMBL5028	O14672	ADAM10	84.11%	97.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.91%	89.62%
CHEMBL202	P00374	Dihydrofolate reductase	82.98%	89.92%
CHEMBL255	P29275	Adenosine A2b receptor	82.68%	98.59%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	82.52%	81.88%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.52%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.50%	95.89%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	81.31%	82.86%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.35%	98.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.30%	97.50%

Plants that contains it

• Ipomoea purpurea
• Jacquemontia tamnifolia

Cross-Links

• PubChem: 5486180
• LOTUS: LTS0263133
• wikiData: Q15633935