(9R,12R,14S,16S,17S,18S)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol

Details

• Internal ID: 01795343-1ba7-4b6d-8da3-be0c00f767e4
• Taxonomy: Alkaloids and derivatives > Ajmaline-sarpagine alkaloids
• IUPAC Name: (9R,12R,14S,16S,17S,18S)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol
• SMILES (Canonical): CCC1C2CC3C4C5(CC(C2C5O)N3C1O)C6=CC=CC=C6N4C
• SMILES (Isomeric): CCC1[C@@H]2CC3[C@H]4C5(C[C@@H]([C@H]2[C@@H]5O)N3[C@H]1O)C6=CC=CC=C6N4C
• InChI: InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10?,11-,14?,15-,16-,17-,18-,19-,20?/m0/s1
• InChI Key: CJDRUOGAGYHKKD-XJHJYMQISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₂O₂
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.199428076 g/mol
• Topological Polar Surface Area (TPSA): 46.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9499	94.99%
Caco-2	+	0.7783	77.83%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7372	73.72%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.9032	90.32%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6419	64.19%
P-glycoprotein inhibitior	-	0.8669	86.69%
P-glycoprotein substrate	+	0.5333	53.33%
CYP3A4 substrate	-	0.5350	53.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4425	44.25%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6431	64.31%
CYP inhibitory promiscuity	-	0.5565	55.65%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6066	60.66%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9853	98.53%
Skin irritation	-	0.8002	80.02%
Skin corrosion	-	0.9272	92.72%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6704	67.04%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	-	0.8509	85.09%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7631	76.31%
Acute Oral Toxicity (c)	II	0.7280	72.80%
Estrogen receptor binding	+	0.6850	68.50%
Androgen receptor binding	+	0.6421	64.21%
Thyroid receptor binding	+	0.6726	67.26%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.6515	65.15%
PPAR gamma	+	0.5552	55.52%
Honey bee toxicity	-	0.8970	89.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.7597	75.97%

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	98.28%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.76%	98.95%
CHEMBL4208	P20618	Proteasome component C5	88.42%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.20%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.40%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	83.84%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.93%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.73%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.54%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.31%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.24%	82.69%

Plants that contains it

• Rauvolfia linearifolia
• Rauvolfia semperflorens
• Rauvolfia serpentina

Cross-Links

• PubChem: 101660347
• LOTUS: LTS0181772
• wikiData: Q104252745