(6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-[(2S)-2-methylbutyl]-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

Details

• Internal ID: 9ed5e77b-04b0-4b7a-9669-961943a7edfe
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-[(2S)-2-methylbutyl]-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/C33H43N5O5/c1-6-19(4)13-26-30(40)37-12-8-11-27(37)33(42)38(26)31(41)32(43-33,18(2)3)35-29(39)21-14-23-22-9-7-10-24-28(22)20(16-34-24)15-25(23)36(5)17-21/h7,9-10,14,16,18-19,21,25-27,34,42H,6,8,11-13,15,17H2,1-5H3,(H,35,39)/t19-,21+,25+,26-,27-,32+,33-/m0/s1
• InChI Key: YWUPWZLPDBNQNZ-WJNFXZNMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₃N₅O₅
• Molecular Weight: 589.70 g/mol
• Exact Mass: 589.32641949 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.8050	80.50%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.3077	30.77%
OATP2B1 inhibitior	+	0.5727	57.27%
OATP1B1 inhibitior	+	0.8629	86.29%
OATP1B3 inhibitior	+	0.9088	90.88%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9641	96.41%
P-glycoprotein inhibitior	+	0.9081	90.81%
P-glycoprotein substrate	+	0.6812	68.12%
CYP3A4 substrate	+	0.7865	78.65%
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	+	0.6138	61.38%
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	-	0.9552	95.52%
Skin irritation	-	0.7455	74.55%
Skin corrosion	-	0.9240	92.40%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6766	67.66%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.7727	77.27%
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	-	0.7434	74.34%
Acute Oral Toxicity (c)	III	0.6087	60.87%
Estrogen receptor binding	+	0.8554	85.54%
Androgen receptor binding	+	0.8038	80.38%
Thyroid receptor binding	+	0.5505	55.05%
Glucocorticoid receptor binding	+	0.7670	76.70%
Aromatase binding	+	0.8143	81.43%
PPAR gamma	+	0.8549	85.49%
Honey bee toxicity	-	0.7686	76.86%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5350	53.50%
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	99.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.15%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.57%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	94.77%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.77%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.64%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.32%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.11%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.57%	89.00%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	91.18%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.10%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.35%	93.56%
CHEMBL217	P14416	Dopamine D2 receptor	90.21%	95.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.67%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.87%	94.45%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	87.64%	98.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.62%	90.08%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.34%	97.50%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.17%	98.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.51%	94.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.26%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.24%	85.14%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.03%	83.10%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.93%	96.77%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.52%	97.64%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.43%	99.18%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.26%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.61%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.05%	96.21%
CHEMBL3524	P56524	Histone deacetylase 4	81.90%	92.97%
CHEMBL3837	P07711	Cathepsin L	81.75%	96.61%
CHEMBL4208	P20618	Proteasome component C5	81.48%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.44%	89.62%
CHEMBL255	P29275	Adenosine A2b receptor	81.34%	98.59%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.07%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101667665
• LOTUS: LTS0055206
• wikiData: Q105367352