(1R,10S,12R,13R,16R,17S)-16-methyl-15-oxa-8,19-diazahexacyclo[11.8.0.01,9.02,7.010,19.012,17]henicosa-2,4,6,8-tetraene

Details

• Internal ID: 6090c456-a4ea-4367-b928-e22b81a520be
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: (1R,10S,12R,13R,16R,17S)-16-methyl-15-oxa-8,19-diazahexacyclo[11.8.0.01,9.02,7.010,19.012,17]henicosa-2,4,6,8-tetraene
• SMILES (Canonical): CC1C2CN3CCC45C(C2CC3C4=NC6=CC=CC=C56)CO1
• SMILES (Isomeric): C[C@@H]1[C@@H]2CN3CC[C@]45[C@@H]([C@H]2C[C@H]3C4=NC6=CC=CC=C56)CO1
• InChI: InChI=1S/C19H22N2O/c1-11-13-9-21-7-6-19-14-4-2-3-5-16(14)20-18(19)17(21)8-12(13)15(19)10-22-11/h2-5,11-13,15,17H,6-10H2,1H3/t11-,12+,13+,15-,17+,19+/m1/s1
• InChI Key: IZMNRMSNPWCOTC-PDVYZHLNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.173213330 g/mol
• Topological Polar Surface Area (TPSA): 24.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	+	0.8996	89.96%
Blood Brain Barrier	+	0.9379	93.79%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.5641	56.41%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.9286	92.86%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6363	63.63%
P-glycoprotein inhibitior	-	0.8808	88.08%
P-glycoprotein substrate	+	0.6582	65.82%
CYP3A4 substrate	+	0.6475	64.75%
CYP2C9 substrate	-	0.7891	78.91%
CYP2D6 substrate	+	0.4236	42.36%
CYP3A4 inhibition	-	0.5337	53.37%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.8075	80.75%
CYP2D6 inhibition	+	0.5247	52.47%
CYP1A2 inhibition	-	0.6809	68.09%
CYP2C8 inhibition	-	0.6381	63.81%
CYP inhibitory promiscuity	-	0.7657	76.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6359	63.59%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.9894	98.94%
Skin irritation	-	0.7395	73.95%
Skin corrosion	-	0.8338	83.38%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7835	78.35%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5806	58.06%
skin sensitisation	-	0.8075	80.75%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5459	54.59%
Acute Oral Toxicity (c)	III	0.6202	62.02%
Estrogen receptor binding	-	0.5526	55.26%
Androgen receptor binding	+	0.7299	72.99%
Thyroid receptor binding	+	0.5951	59.51%
Glucocorticoid receptor binding	-	0.7702	77.02%
Aromatase binding	-	0.6546	65.46%
PPAR gamma	-	0.6611	66.11%
Honey bee toxicity	-	0.8130	81.30%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.6708	67.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.77%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.90%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	90.20%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.13%	95.56%
CHEMBL238	Q01959	Dopamine transporter	83.22%	95.88%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.64%	96.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.29%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.00%	91.11%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.78%	89.62%
CHEMBL5028	O14672	ADAM10	80.56%	97.50%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	80.11%	98.33%

Plants that contains it

• Tabernaemontana divaricata

Cross-Links

• PubChem: 162939603
• LOTUS: LTS0248025
• wikiData: Q104888962