(5alpha)-9,10-Didehydro-6-methylergoline-8beta-methanol

Details

• Internal ID: 230246a6-0f28-4b11-8e90-297413fe5d45
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Clavines and derivatives
• IUPAC Name: [(6aS,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol
• SMILES (Canonical): CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)CO
• SMILES (Isomeric): CN1C[C@@H](C=C2[C@@H]1CC3=CNC4=CC=CC2=C34)CO
• InChI: InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15+/m1/s1
• InChI Key: BIXJFIJYBLJTMK-BMIGLBTASA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈N₂O
• Molecular Weight: 254.33 g/mol
• Exact Mass: 254.141913202 g/mol
• Topological Polar Surface Area (TPSA): 39.30 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• NCGC00016520-01
• CAS-602-85-7
• (5alpha)-9,10-Didehydro-6-methylergoline-8beta-methanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9607	96.07%
Caco-2	+	0.7800	78.00%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Lysosomes	0.3945	39.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9405	94.05%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.5783	57.83%
P-glycoprotein inhibitior	-	0.9584	95.84%
P-glycoprotein substrate	+	0.6798	67.98%
CYP3A4 substrate	+	0.6833	68.33%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	+	0.5841	58.41%
CYP3A4 inhibition	-	0.8832	88.32%
CYP2C9 inhibition	-	0.9120	91.20%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.8690	86.90%
CYP inhibitory promiscuity	-	0.8629	86.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6403	64.03%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9958	99.58%
Skin irritation	-	0.7390	73.90%
Skin corrosion	-	0.8855	88.55%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7872	78.72%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8412	84.12%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7482	74.82%
Acute Oral Toxicity (c)	III	0.5873	58.73%
Estrogen receptor binding	+	0.6489	64.89%
Androgen receptor binding	+	0.6442	64.42%
Thyroid receptor binding	-	0.5836	58.36%
Glucocorticoid receptor binding	+	0.5933	59.33%
Aromatase binding	-	0.6457	64.57%
PPAR gamma	-	0.5197	51.97%
Honey bee toxicity	-	0.9219	92.19%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8537	85.37%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	12589.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	10000 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	3981.07 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	125.89 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	14125.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.06%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.08%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.75%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL217	P14416	Dopamine D2 receptor	91.85%	95.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.83%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.30%	97.25%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	85.60%	96.39%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.74%	82.69%
CHEMBL1907	P15144	Aminopeptidase N	83.67%	93.31%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.45%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.69%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.54%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.38%	86.33%
CHEMBL2535	P11166	Glucose transporter	80.57%	98.75%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.03%	96.25%

Plants that contains it

• Ipomoea nil

Cross-Links

• PubChem: 6604277
• NPASS: NPC37423
• ChEMBL: CHEMBL1331189