(9S)-N-[2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-5,5a,6,6a,8,9-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Details

• Internal ID: 0a9d95f6-fb5a-4d42-a9bc-482cf698c0af
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (9S)-N-[2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-5,5a,6,6a,8,9-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• SMILES (Canonical): CC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6CNC7=CC=CC(=C67)C5=C4)C)O
• SMILES (Isomeric): CC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)[C@@H]4CN(C5CC6CNC7=CC=CC(=C67)C5=C4)C)O
• InChI: InChI=1S/C31H41N5O5/c1-16(2)26-28(38)35-11-7-10-24(35)31(40)36(26)29(39)30(41-31,17(3)4)33-27(37)19-12-21-20-8-6-9-22-25(20)18(14-32-22)13-23(21)34(5)15-19/h6,8-9,12,16-19,23-24,26,32,40H,7,10-11,13-15H2,1-5H3,(H,33,37)/t18?,19-,23?,24?,26?,30?,31?/m0/s1
• InChI Key: XVONYJCXGKLAJK-LLNLXBAJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₁N₅O₅
• Molecular Weight: 563.70 g/mol
• Exact Mass: 563.31076943 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9377	93.77%
Caco-2	-	0.7966	79.66%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Nucleus	0.3526	35.26%
OATP2B1 inhibitior	-	0.7092	70.92%
OATP1B1 inhibitior	+	0.8700	87.00%
OATP1B3 inhibitior	+	0.9175	91.75%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8265	82.65%
P-glycoprotein inhibitior	+	0.6752	67.52%
P-glycoprotein substrate	+	0.7206	72.06%
CYP3A4 substrate	+	0.7528	75.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7446	74.46%
CYP3A4 inhibition	+	0.5140	51.40%
CYP2C9 inhibition	-	0.8497	84.97%
CYP2C19 inhibition	-	0.6145	61.45%
CYP2D6 inhibition	-	0.9125	91.25%
CYP1A2 inhibition	+	0.5212	52.12%
CYP2C8 inhibition	+	0.5747	57.47%
CYP inhibitory promiscuity	-	0.8660	86.60%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5351	53.51%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9535	95.35%
Skin irritation	-	0.7317	73.17%
Skin corrosion	-	0.9225	92.25%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.5599	55.99%
skin sensitisation	-	0.8512	85.12%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6585	65.85%
Acute Oral Toxicity (c)	III	0.6176	61.76%
Estrogen receptor binding	+	0.8145	81.45%
Androgen receptor binding	+	0.6999	69.99%
Thyroid receptor binding	+	0.5504	55.04%
Glucocorticoid receptor binding	+	0.7600	76.00%
Aromatase binding	+	0.7256	72.56%
PPAR gamma	+	0.7433	74.33%
Honey bee toxicity	-	0.7884	78.84%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9794	97.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.62%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.30%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.51%	97.25%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	95.68%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.05%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.41%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.30%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.19%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.28%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.25%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.56%	97.09%
CHEMBL3524	P56524	Histone deacetylase 4	91.46%	92.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.44%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.08%	96.38%
CHEMBL1951	P21397	Monoamine oxidase A	89.63%	91.49%
CHEMBL4208	P20618	Proteasome component C5	89.35%	90.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.62%	95.58%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	86.80%	98.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.63%	93.56%
CHEMBL301	P24941	Cyclin-dependent kinase 2	86.58%	91.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.32%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.72%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.33%	96.77%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.47%	90.08%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.89%	92.88%
CHEMBL340	P08684	Cytochrome P450 3A4	82.78%	91.19%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.11%	95.69%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	81.49%	95.34%
CHEMBL4072	P07858	Cathepsin B	81.46%	93.67%
CHEMBL4805	Q99572	P2X purinoceptor 7	80.78%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.41%	97.14%

Plants that contains it

• Ipomoea cairica

Cross-Links

• PubChem: 5317163
• NPASS: NPC231056
• LOTUS: LTS0044503
• wikiData: Q105343032