Ergobutyrine

Details

• Internal ID: 4ee98840-a463-40cc-8a53-77da8fa0c041
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7R)-7-ethyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-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
• InChI: InChI=1S/C30H37N5O5/c1-5-22-27(37)34-11-7-10-24(34)30(39)35(22)28(38)29(40-30,16(2)3)32-26(36)18-12-20-19-8-6-9-21-25(19)17(14-31-21)13-23(20)33(4)15-18/h6,8-9,12,14,16,18,22-24,31,39H,5,7,10-11,13,15H2,1-4H3,(H,32,36)/t18-,22-,23-,24+,29-,30+/m1/s1
• InChI Key: LWEABIUVMWANJF-UMRLHMAQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₇N₅O₅
• Molecular Weight: 547.60 g/mol
• Exact Mass: 547.27946930 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Ergobutyrine
• Ergotaman-3',6',18-trione, 5'-ethyl-12'-hydroxy-2'-(1-methylethyl)-, (5'alpha)-
• DTXSID501002789
• N-[5-Ethyl-10b-hydroxy-3,6-dioxo-2-(propan-2-yl)octahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-6-methyl-9,10-didehydroergoline-8-carboximidic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.8069	80.69%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.9571	95.71%
Subcellular localzation	Mitochondria	0.3077	30.77%
OATP2B1 inhibitior	-	0.5678	56.78%
OATP1B1 inhibitior	+	0.8578	85.78%
OATP1B3 inhibitior	+	0.9088	90.88%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9484	94.84%
P-glycoprotein inhibitior	+	0.7909	79.09%
P-glycoprotein substrate	+	0.6712	67.12%
CYP3A4 substrate	+	0.7875	78.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.8835	88.35%
CYP2C9 inhibition	-	0.8937	89.37%
CYP2C19 inhibition	-	0.7552	75.52%
CYP2D6 inhibition	-	0.9195	91.95%
CYP1A2 inhibition	+	0.8638	86.38%
CYP2C8 inhibition	+	0.5721	57.21%
CYP inhibitory promiscuity	-	0.6370	63.70%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5024	50.24%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9620	96.20%
Skin irritation	-	0.7455	74.55%
Skin corrosion	-	0.9240	92.40%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6963	69.63%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.7513	75.13%
skin sensitisation	-	0.8662	86.62%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7624	76.24%
Acute Oral Toxicity (c)	III	0.6087	60.87%
Estrogen receptor binding	+	0.8392	83.92%
Androgen receptor binding	+	0.7955	79.55%
Thyroid receptor binding	+	0.5280	52.80%
Glucocorticoid receptor binding	+	0.7538	75.38%
Aromatase binding	+	0.8059	80.59%
PPAR gamma	+	0.8184	81.84%
Honey bee toxicity	-	0.7854	78.54%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9912	99.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.86%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.67%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.69%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	96.05%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.74%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.77%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.41%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.13%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.01%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	91.83%	95.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.43%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.35%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.76%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.39%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.11%	90.08%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.71%	98.05%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.57%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.36%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.99%	94.45%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.94%	83.10%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	86.82%	98.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.80%	96.47%
CHEMBL3524	P56524	Histone deacetylase 4	86.63%	92.97%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	86.39%	97.64%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	85.30%	95.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.77%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.21%	96.77%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.84%	95.71%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.46%	99.18%
CHEMBL4208	P20618	Proteasome component C5	83.08%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	83.05%	98.59%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.07%	88.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.88%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.28%	89.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.07%	95.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 158175
• LOTUS: LTS0163387
• wikiData: Q82997061