methyl (1R,15S,20S)-6,7-dimethoxy-16-methylidene-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Details

• Internal ID: 86256761-247c-42f4-bf55-00f693f0e2a6
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1R,15S,20S)-6,7-dimethoxy-16-methylidene-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• SMILES (Canonical): COC1=C(C=C2C(=C1)C3=C(N2)C4CC5C(CN4CC3)C(=C)OC=C5C(=O)OC)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C3=C(N2)[C@H]4C[C@H]5[C@@H](CN4CC3)C(=C)OC=C5C(=O)OC)OC
• InChI: InChI=1S/C23H26N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h8-9,11,14,16,19,24H,1,5-7,10H2,2-4H3/t14-,16-,19+/m0/s1
• InChI Key: RMQMNQMSKODSEY-URLQWDBASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆N₂O₅
• Molecular Weight: 410.50 g/mol
• Exact Mass: 410.18417193 g/mol
• Topological Polar Surface Area (TPSA): 73.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.32
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9622	96.22%
Caco-2	+	0.6376	63.76%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5647	56.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.8456	84.56%
MATE1 inhibitior	-	0.8219	82.19%
OCT2 inhibitior	-	0.5639	56.39%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	+	0.5927	59.27%
P-glycoprotein substrate	+	0.7467	74.67%
CYP3A4 substrate	+	0.6724	67.24%
CYP2C9 substrate	-	0.6054	60.54%
CYP2D6 substrate	+	0.3933	39.33%
CYP3A4 inhibition	-	0.5345	53.45%
CYP2C9 inhibition	-	0.7101	71.01%
CYP2C19 inhibition	-	0.8459	84.59%
CYP2D6 inhibition	-	0.6906	69.06%
CYP1A2 inhibition	+	0.7784	77.84%
CYP2C8 inhibition	+	0.6012	60.12%
CYP inhibitory promiscuity	+	0.5318	53.18%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.7552	75.52%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	+	0.5322	53.22%
Human Ether-a-go-go-Related Gene inhibition	+	0.7280	72.80%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	-	0.8552	85.52%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6572	65.72%
Acute Oral Toxicity (c)	III	0.5816	58.16%
Estrogen receptor binding	-	0.4851	48.51%
Androgen receptor binding	+	0.6844	68.44%
Thyroid receptor binding	+	0.5376	53.76%
Glucocorticoid receptor binding	+	0.7606	76.06%
Aromatase binding	-	0.6256	62.56%
PPAR gamma	-	0.4866	48.66%
Honey bee toxicity	-	0.8439	84.39%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9655	96.55%

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	98.67%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.81%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.68%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.46%	91.11%
CHEMBL2535	P11166	Glucose transporter	91.35%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.71%	85.14%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	89.01%	91.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.51%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.13%	90.71%
CHEMBL255	P29275	Adenosine A2b receptor	85.97%	98.59%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.70%	89.50%
CHEMBL4302	P08183	P-glycoprotein 1	85.15%	92.98%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.97%	97.09%
CHEMBL5747	Q92793	CREB-binding protein	84.95%	95.12%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.93%	90.95%
CHEMBL340	P08684	Cytochrome P450 3A4	83.14%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.97%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.75%	89.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.50%	95.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.38%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.20%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.16%	93.99%
CHEMBL5028	O14672	ADAM10	81.15%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.91%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.51%	95.89%

Plants that contains it

• Rauvolfia grandiflora

Cross-Links

• PubChem: 15907469
• LOTUS: LTS0266693
• wikiData: Q105241004