(6aR,9R)-N-[(1S,2S,4R,7S)-2-methoxy-7-(2-methylpropyl)-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: a6641d90-17f2-4b8d-b37c-0d748425c859
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7S)-2-methoxy-7-(2-methylpropyl)-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
• SMILES (Canonical): CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)OC
• SMILES (Isomeric): CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)OC
• InChI: InChI=1S/C33H43N5O5/c1-18(2)13-26-30(40)37-12-8-11-27(37)33(42-6)38(26)31(41)32(43-33,19(3)4)35-29(39)21-14-23-22-9-7-10-24-28(22)20(16-34-24)15-25(23)36(5)17-21/h7,9-10,14,16,18-19,21,25-27,34H,8,11-13,15,17H2,1-6H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
• InChI Key: IBKONBFVCDMGDA-VFGNJEKYSA-N
• Popularity: 0 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): 107.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 6
• 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	+	0.9639	96.39%
Caco-2	-	0.7872	78.72%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.3322	33.22%
OATP2B1 inhibitior	-	0.7038	70.38%
OATP1B1 inhibitior	+	0.8663	86.63%
OATP1B3 inhibitior	+	0.9072	90.72%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9476	94.76%
P-glycoprotein inhibitior	+	0.9164	91.64%
P-glycoprotein substrate	+	0.7196	71.96%
CYP3A4 substrate	+	0.7850	78.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.9329	93.29%
CYP2C9 inhibition	-	0.8097	80.97%
CYP2C19 inhibition	-	0.6938	69.38%
CYP2D6 inhibition	-	0.8782	87.82%
CYP1A2 inhibition	+	0.7050	70.50%
CYP2C8 inhibition	+	0.6025	60.25%
CYP inhibitory promiscuity	+	0.5580	55.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4578	45.78%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9524	95.24%
Skin irritation	-	0.7575	75.75%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7045	70.45%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.7727	77.27%
skin sensitisation	-	0.8795	87.95%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6282	62.82%
Acute Oral Toxicity (c)	III	0.6175	61.75%
Estrogen receptor binding	+	0.8523	85.23%
Androgen receptor binding	+	0.7916	79.16%
Thyroid receptor binding	+	0.5812	58.12%
Glucocorticoid receptor binding	+	0.7779	77.79%
Aromatase binding	+	0.7921	79.21%
PPAR gamma	+	0.8331	83.31%
Honey bee toxicity	-	0.7239	72.39%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5641	56.41%
Fish aquatic toxicity	+	0.9944	99.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.80%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.95%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.06%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.54%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	95.48%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.36%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.22%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.71%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.82%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.60%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.49%	82.69%
CHEMBL3524	P56524	Histone deacetylase 4	89.49%	92.97%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.19%	90.08%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.00%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.33%	89.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	88.03%	98.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.66%	99.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.48%	93.56%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	86.43%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.90%	94.45%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	85.55%	98.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.30%	96.47%
CHEMBL5747	Q92793	CREB-binding protein	84.85%	95.12%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.09%	99.18%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.05%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.76%	95.71%
CHEMBL2535	P11166	Glucose transporter	82.91%	98.75%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.89%	97.50%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.84%	96.39%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.80%	88.56%
CHEMBL217	P14416	Dopamine D2 receptor	82.36%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.66%	86.33%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	81.60%	97.64%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.15%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.12%	96.77%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.05%	89.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.75%	90.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.47%	97.14%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 13996814
• LOTUS: LTS0248621
• wikiData: Q105036558