methyl (15R)-6-methoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate

Details

• Internal ID: 766f97e3-c2c0-4738-b487-e1cb845d544c
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (15R)-6-methoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate
• SMILES (Canonical): CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=C4C=CC(=C5)OC
• SMILES (Isomeric): CC1[C@H]2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=C4C=CC(=C5)OC
• InChI: InChI=1S/C22H26N2O4/c1-12-17-10-24-7-6-15-14-5-4-13(26-2)8-19(14)23-21(15)20(24)9-16(17)18(11-28-12)22(25)27-3/h4-5,8,11-12,16-17,20,23H,6-7,9-10H2,1-3H3/t12?,16?,17-,20?/m1/s1
• InChI Key: KXEMQEGRZWUKJS-XPIBTUSGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆N₂O₄
• Molecular Weight: 382.50 g/mol
• Exact Mass: 382.18925731 g/mol
• Topological Polar Surface Area (TPSA): 63.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• NSC606024
• SCHEMBL15384592
• NSC-606024

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9776	97.76%
Caco-2	+	0.8359	83.59%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Lysosomes	0.4460	44.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8155	81.55%
OATP1B3 inhibitior	+	0.8648	86.48%
MATE1 inhibitior	-	0.8037	80.37%
OCT2 inhibitior	-	0.5639	56.39%
BSEP inhibitior	+	0.8951	89.51%
P-glycoprotein inhibitior	+	0.7366	73.66%
P-glycoprotein substrate	+	0.6338	63.38%
CYP3A4 substrate	+	0.6949	69.49%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	+	0.3485	34.85%
CYP3A4 inhibition	-	0.6443	64.43%
CYP2C9 inhibition	-	0.6013	60.13%
CYP2C19 inhibition	-	0.9094	90.94%
CYP2D6 inhibition	+	0.5677	56.77%
CYP1A2 inhibition	+	0.8086	80.86%
CYP2C8 inhibition	+	0.6143	61.43%
CYP inhibitory promiscuity	-	0.5547	55.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6220	62.20%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9880	98.80%
Skin irritation	-	0.7722	77.22%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8825	88.25%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6765	67.65%
Acute Oral Toxicity (c)	III	0.6151	61.51%
Estrogen receptor binding	+	0.6387	63.87%
Androgen receptor binding	+	0.8043	80.43%
Thyroid receptor binding	+	0.6320	63.20%
Glucocorticoid receptor binding	+	0.7691	76.91%
Aromatase binding	-	0.7367	73.67%
PPAR gamma	-	0.5807	58.07%
Honey bee toxicity	-	0.8418	84.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9615	96.15%

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	98.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.22%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.33%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	94.42%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.58%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.14%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.72%	95.56%
CHEMBL2535	P11166	Glucose transporter	88.54%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.69%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.64%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	85.27%	95.12%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.90%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.14%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.86%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.36%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.78%	86.92%
CHEMBL340	P08684	Cytochrome P450 3A4	82.58%	91.19%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.12%	90.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.87%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.61%	100.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	81.41%	91.79%
CHEMBL5028	O14672	ADAM10	80.87%	97.50%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.58%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.57%	95.89%

Plants that contains it

• Rauvolfia vomitoria

Cross-Links

• PubChem: 354380
• LOTUS: LTS0005921
• wikiData: Q105147306