Ergotamine

Details

• Internal ID: eb74a0f2-c5e9-4ab9-9376-6aea75cd3e8e
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines > Ergotamines, dihydroergotamines, and derivatives
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• SMILES (Canonical): CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN(C6CC7=CNC8=CC=CC(=C78)C6=C5)C
• SMILES (Isomeric): C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C
• InChI: InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
• InChI Key: XCGSFFUVFURLIX-VFGNJEKYSA-N
• Popularity: 7,066 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₅N₅O₅
• Molecular Weight: 581.70 g/mol
• Exact Mass: 581.26381923 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Ergotamin
• Gynergen
• Ergonsvine
• Ergostat
• ergotamine tartrate
• ergotaminum
• Ergotamina
• Ergomar
• 113-15-5
• Ergotaminum [INN-Latin]
• Ergotamina [INN-Spanish]
• Rigetamin
• HSDB 4076
• 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
• Ergotamine bitartrate
• EINECS 204-023-9
• NSC 95090
• Ergotamine (INN)
• UNII-PR834Q503T
• BRN 0078890
• CHEBI:64318
• PR834Q503T
• NSC-95090
• DTXSID9043774
• ergopeptine
• ERGOTAMINE [INN]
• Ergotaminum (INN-Latin)
• Ergotamina (INN-Spanish)
• (5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
• Ergotamine [INN:BAN]
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-
• (5'alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
• (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• 379-79-3
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) (salt)
• ERM
• Ergotaminum (Latin)
• Ergotamin; ergotaminum
• NSC41869
• ERGOTAMINE [MI]
• ERGOTAMINE [HSDB]
• ERGOTAMINE [VANDF]
• CHEMBL442
• SCHEMBL1483
• ERGOTAMINE [WHO-DD]
• GTPL149
• DTXCID7023774
• N02CA02
• Ergotamine tartrate, Avetol, Cornutamin, Ergam, Ergotartrate
• HMS2089H22
• BDBM50027065
• Ergotamine dried down 100 microg/mL
• AKOS015896505
• DB00696
• NCGC00356592-02
• D07906
• AB01275473-01
• Q419186
• CODERGOCRINE MESILATE IMPURITY C [EP IMPURITY]
• 5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
• (5''alpha)-12''-hydroxy-2''-methyl-5''-(phenylmethyl)ergotoman-3'',6'',18-trione
• (5''alpha)-5''-benzyl-12''-hydroxy-2''-methyl-3'',6'',18-trioxoergotaman
• (5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione
• (5alpha,5'beta)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
• 12''-hydroxy-2''-methyl-5''alpha-(phenylmethyl)ergotaman-3'',6'',18-trione
• 1080650-16-3
• N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-methyl-[?]carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9621	96.21%
Caco-2	-	0.8399	83.99%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Nucleus	0.3523	35.23%
OATP2B1 inhibitior	-	0.5751	57.51%
OATP1B1 inhibitior	+	0.7308	73.08%
OATP1B3 inhibitior	+	0.9078	90.78%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9776	97.76%
P-glycoprotein inhibitior	+	0.9511	95.11%
P-glycoprotein substrate	+	0.7695	76.95%
CYP3A4 substrate	+	0.7981	79.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.8849	88.49%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.6865	68.65%
CYP inhibitory promiscuity	-	0.6759	67.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5016	50.16%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9565	95.65%
Skin irritation	-	0.7375	73.75%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7968	79.68%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.9608	96.08%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.5646	56.46%
Estrogen receptor binding	+	0.8268	82.68%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5274	52.74%
Glucocorticoid receptor binding	+	0.7991	79.91%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.7843	78.43%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9833	98.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	501.2 nM	Potency	via Super-PRED
CHEMBL1898	P28222	Serotonin 1b (5-HT1b) receptor	2.1 nM	Ki	via Super-PRED
CHEMBL1983	P28221	Serotonin 1d (5-HT1d) receptor	2.2 nM	Ki	via Super-PRED
CHEMBL3426	P47898	Serotonin 5a (5-HT5a) receptor	15.49 nM	Ki	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	446.7 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.89%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.35%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	96.23%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.15%	95.56%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	96.01%	97.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.94%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.44%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	93.74%	95.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	93.32%	93.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.63%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.39%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	91.75%	90.17%
CHEMBL5805	Q9NR97	Toll-like receptor 8	89.52%	96.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.42%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.57%	99.23%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.72%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.16%	86.33%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.90%	92.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.85%	97.09%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	84.68%	95.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.61%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.50%	96.21%
CHEMBL3524	P56524	Histone deacetylase 4	84.31%	92.97%
CHEMBL1902	P62942	FK506-binding protein 1A	83.66%	97.05%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.07%	98.33%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	82.43%	85.83%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.71%	85.11%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.96%	91.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.00%	94.45%

Plants that contains it

• Cenchrus echinatus
• Festuca arundinacea
• Festuca pratensis

Cross-Links

• PubChem: 8223
• LOTUS: LTS0042813
• wikiData: Q419186