(6aR,9S)-N-[(1S)-1-hydroxyethyl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Details

• Internal ID: 32be5a6f-2d82-4a68-bef1-e19e51abd894
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Lysergamides
• IUPAC Name: (6aR,9S)-N-[(1S)-1-hydroxyethyl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• InChI: InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23)/t10-,12-,16+/m0/s1
• InChI Key: WYTJZJPVCDWOOI-KNHMANMVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁N₃O₂
• Molecular Weight: 311.40 g/mol
• Exact Mass: 311.16337692 g/mol
• Topological Polar Surface Area (TPSA): 68.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	-	0.7901	79.01%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5830	58.30%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9373	93.73%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	+	0.8314	83.14%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7419	74.19%
P-glycoprotein inhibitior	-	0.9644	96.44%
P-glycoprotein substrate	+	0.8165	81.65%
CYP3A4 substrate	+	0.7788	77.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7323	73.23%
CYP3A4 inhibition	-	0.7713	77.13%
CYP2C9 inhibition	-	0.8804	88.04%
CYP2C19 inhibition	-	0.8866	88.66%
CYP2D6 inhibition	-	0.5407	54.07%
CYP1A2 inhibition	-	0.5258	52.58%
CYP2C8 inhibition	-	0.8779	87.79%
CYP inhibitory promiscuity	-	0.8968	89.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6455	64.55%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9991	99.91%
Skin irritation	-	0.7720	77.20%
Skin corrosion	-	0.9316	93.16%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6951	69.51%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.6949	69.49%
skin sensitisation	-	0.8699	86.99%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8829	88.29%
Acute Oral Toxicity (c)	III	0.4547	45.47%
Estrogen receptor binding	+	0.6770	67.70%
Androgen receptor binding	+	0.8206	82.06%
Thyroid receptor binding	-	0.7538	75.38%
Glucocorticoid receptor binding	-	0.5913	59.13%
Aromatase binding	-	0.5406	54.06%
PPAR gamma	-	0.5787	57.87%
Honey bee toxicity	-	0.8723	87.23%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9259	92.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.27%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.27%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.88%	91.49%
CHEMBL2535	P11166	Glucose transporter	94.63%	98.75%
CHEMBL217	P14416	Dopamine D2 receptor	93.97%	95.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.41%	93.03%
CHEMBL2094135	Q96BI3	Gamma-secretase	91.30%	98.05%
CHEMBL4073	P09237	Matrix metalloproteinase 7	91.03%	97.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.25%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.07%	93.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.62%	82.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.29%	97.25%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.55%	89.62%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	85.45%	83.10%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.21%	94.45%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.63%	88.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.34%	99.23%
CHEMBL5028	O14672	ADAM10	83.96%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.21%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.19%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.18%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.11%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.61%	85.14%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.06%	97.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.29%	95.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.96%	96.39%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.67%	95.56%

Plants that contains it

• Ipomoea violacea

Cross-Links

• PubChem: 162915534
• LOTUS: LTS0059016
• wikiData: Q105322626