(6aR,9R)-N-[(2R)-1-[(3S,8aR)-3-benzyl-1,4-dioxo-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxobutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Details

• Internal ID: 8ff49d55-52cb-4332-8ecd-9e99f43c3743
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Lysergamides
• IUPAC Name: (6aR,9R)-N-[(2R)-1-[(3S,8aR)-3-benzyl-1,4-dioxo-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxobutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• SMILES (Canonical): CC(C)C(C(=O)N1C(C(=O)N2CCCC2C1=O)CC3=CC=CC=C3)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C
• SMILES (Isomeric): CC(C)[C@H](C(=O)N1[C@H](C(=O)N2CCC[C@@H]2C1=O)CC3=CC=CC=C3)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C
• InChI: InChI=1S/C35H39N5O4/c1-20(2)31(35(44)40-29(15-21-9-5-4-6-10-21)33(42)39-14-8-13-27(39)34(40)43)37-32(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-28(25)38(3)19-23/h4-7,9-12,16,18,20,23,27-29,31,36H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28-,29+,31-/m1/s1
• InChI Key: KMDKLWZQLMBIBS-XJGLHGQXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₉N₅O₄
• Molecular Weight: 593.70 g/mol
• Exact Mass: 593.30020474 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.15
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9784	97.84%
Caco-2	-	0.7993	79.93%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6744	67.44%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.8663	86.63%
OATP1B3 inhibitior	+	0.9235	92.35%
MATE1 inhibitior	+	0.7056	70.56%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9870	98.70%
P-glycoprotein inhibitior	+	0.8910	89.10%
P-glycoprotein substrate	+	0.8478	84.78%
CYP3A4 substrate	+	0.7851	78.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7366	73.66%
CYP3A4 inhibition	-	0.6512	65.12%
CYP2C9 inhibition	-	0.8393	83.93%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9113	91.13%
CYP1A2 inhibition	-	0.6462	64.62%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8489	84.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6093	60.93%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9497	94.97%
Skin irritation	-	0.7695	76.95%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9046	90.46%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.8358	83.58%
skin sensitisation	-	0.8893	88.93%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8312	83.12%
Acute Oral Toxicity (c)	III	0.6425	64.25%
Estrogen receptor binding	+	0.8041	80.41%
Androgen receptor binding	+	0.7691	76.91%
Thyroid receptor binding	+	0.5610	56.10%
Glucocorticoid receptor binding	+	0.7571	75.71%
Aromatase binding	+	0.5557	55.57%
PPAR gamma	+	0.8021	80.21%
Honey bee toxicity	-	0.7962	79.62%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5359	53.59%
Fish aquatic toxicity	+	0.9731	97.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.93%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.23%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.70%	95.56%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.62%	97.64%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	95.52%	93.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.44%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.62%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.95%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.23%	96.47%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	92.12%	98.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.51%	90.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.82%	97.25%
CHEMBL2535	P11166	Glucose transporter	90.40%	98.75%
CHEMBL3524	P56524	Histone deacetylase 4	90.02%	92.97%
CHEMBL333	P08253	Matrix metalloproteinase-2	89.33%	96.31%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	88.13%	97.50%
CHEMBL1951	P21397	Monoamine oxidase A	87.39%	91.49%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	86.83%	91.43%
CHEMBL221	P23219	Cyclooxygenase-1	86.73%	90.17%
CHEMBL4072	P07858	Cathepsin B	86.43%	93.67%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.89%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.78%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.19%	97.09%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.76%	99.18%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	84.76%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.58%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.18%	89.00%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	82.54%	85.83%
CHEMBL5028	O14672	ADAM10	82.51%	97.50%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.07%	96.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.50%	90.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.37%	88.56%
CHEMBL217	P14416	Dopamine D2 receptor	80.06%	95.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163185312
• LOTUS: LTS0247271
• wikiData: Q105142930