(6aR,9S)-N-[(1S,4R,7S)-2-hydroxy-4-methyl-7-(2-methylpropyl)-5,8-dioxo-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: 89752cab-56e1-440b-88b5-1f3379b35247
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (6aR,9S)-N-[(1S,4R,7S)-2-hydroxy-4-methyl-7-(2-methylpropyl)-5,8-dioxo-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)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
• SMILES (Isomeric): CC(C)C[C@H]1C(=O)N2CCC[C@H]2C3(N1C(=O)[C@](O3)(C)NC(=O)[C@@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
• InChI: InChI=1S/C30H37N5O5/c1-16(2)11-23-27(37)34-10-6-9-24(34)30(39)35(23)28(38)29(3,40-30)32-26(36)18-12-20-19-7-5-8-21-25(19)17(14-31-21)13-22(20)33(4)15-18/h5,7-8,12,14,16,18,22-24,31,39H,6,9-11,13,15H2,1-4H3,(H,32,36)/t18-,22+,23-,24-,29+,30?/m0/s1
• InChI Key: NESVMZOPWPCFAU-FEPBCZIASA-N
• Popularity: 0 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: 1.80
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 6
• 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	+	0.9592	95.92%
Caco-2	-	0.8077	80.77%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.9571	95.71%
Subcellular localzation	Nucleus	0.3901	39.01%
OATP2B1 inhibitior	-	0.5676	56.76%
OATP1B1 inhibitior	+	0.8294	82.94%
OATP1B3 inhibitior	+	0.9050	90.50%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8732	87.32%
P-glycoprotein inhibitior	+	0.9035	90.35%
P-glycoprotein substrate	+	0.7222	72.22%
CYP3A4 substrate	+	0.7931	79.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.8487	84.87%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.7688	76.88%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.5867	58.67%
CYP inhibitory promiscuity	-	0.6627	66.27%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4969	49.69%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9609	96.09%
Skin irritation	-	0.7415	74.15%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3749	37.49%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.8286	82.86%
skin sensitisation	-	0.8673	86.73%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8233	82.33%
Acute Oral Toxicity (c)	III	0.6051	60.51%
Estrogen receptor binding	+	0.8401	84.01%
Androgen receptor binding	+	0.8272	82.72%
Thyroid receptor binding	+	0.5370	53.70%
Glucocorticoid receptor binding	+	0.7978	79.78%
Aromatase binding	+	0.7683	76.83%
PPAR gamma	+	0.8224	82.24%
Honey bee toxicity	-	0.7788	77.88%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5541	55.41%
Fish aquatic toxicity	+	0.9882	98.82%

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%
CHEMBL1951	P21397	Monoamine oxidase A	97.26%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.56%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.13%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.91%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.87%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.81%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.55%	82.69%
CHEMBL217	P14416	Dopamine D2 receptor	92.99%	95.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.20%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.10%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.82%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.54%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.94%	93.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.61%	85.14%
CHEMBL3524	P56524	Histone deacetylase 4	88.73%	92.97%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	88.34%	95.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	88.26%	98.33%
CHEMBL4073	P09237	Matrix metalloproteinase 7	88.05%	97.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.59%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.51%	96.21%
CHEMBL2094135	Q96BI3	Gamma-secretase	86.93%	98.05%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	86.74%	97.64%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.27%	90.08%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.13%	97.50%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.91%	85.11%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.46%	88.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.31%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.86%	94.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.87%	83.10%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.44%	95.71%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.14%	99.18%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.61%	100.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.76%	96.39%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.05%	96.77%
CHEMBL2514	O95665	Neurotensin receptor 2	80.45%	100.00%

Plants that contains it

• Ipomoea tricolor
• Jacquemontia tamnifolia
• Lolium arundinaceum

Cross-Links

• PubChem: 5317170
• LOTUS: LTS0046308
• wikiData: Q105178167