(1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2(7),3,5-triene-6,14,18-triol

Details

• Internal ID: b953c60c-1989-4d98-9f98-a9b6cee7007d
• Taxonomy: Alkaloids and derivatives > Ajmaline-sarpagine alkaloids
• IUPAC Name: (1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2(7),3,5-triene-6,14,18-triol
• SMILES (Canonical): CCC1C2CC3C4C5(CC(C2C5O)N3C1O)C6=C(N4C)C(=CC=C6)O
• SMILES (Isomeric): CC[C@H]1[C@@H]2C[C@H]3[C@H]4[C@@]5(C[C@@H]([C@H]2[C@H]5O)N3[C@@H]1O)C6=C(N4C)C(=CC=C6)O
• InChI: InChI=1S/C20H26N2O3/c1-3-9-10-7-12-17-20(11-5-4-6-14(23)16(11)21(17)2)8-13(15(10)18(20)24)22(12)19(9)25/h4-6,9-10,12-13,15,17-19,23-25H,3,7-8H2,1-2H3/t9-,10-,12-,13-,15-,17-,18+,19+,20+/m0/s1
• InChI Key: RAGDTPVHROXSDN-IWCYVRMPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₂O₃
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.19434270 g/mol
• Topological Polar Surface Area (TPSA): 67.20 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9389	93.89%
Caco-2	+	0.6449	64.49%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8016	80.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9395	93.95%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.7473	74.73%
P-glycoprotein inhibitior	-	0.8871	88.71%
P-glycoprotein substrate	+	0.6593	65.93%
CYP3A4 substrate	+	0.5413	54.13%
CYP2C9 substrate	-	0.8465	84.65%
CYP2D6 substrate	+	0.4301	43.01%
CYP3A4 inhibition	-	0.8143	81.43%
CYP2C9 inhibition	-	0.8055	80.55%
CYP2C19 inhibition	-	0.7123	71.23%
CYP2D6 inhibition	+	0.7623	76.23%
CYP1A2 inhibition	-	0.8456	84.56%
CYP2C8 inhibition	-	0.6022	60.22%
CYP inhibitory promiscuity	+	0.5994	59.94%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6340	63.40%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9752	97.52%
Skin irritation	-	0.8030	80.30%
Skin corrosion	-	0.9334	93.34%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4497	44.97%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6670	66.70%
skin sensitisation	-	0.8557	85.57%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7475	74.75%
Acute Oral Toxicity (c)	II	0.5471	54.71%
Estrogen receptor binding	+	0.6900	69.00%
Androgen receptor binding	+	0.6688	66.88%
Thyroid receptor binding	+	0.6811	68.11%
Glucocorticoid receptor binding	-	0.7366	73.66%
Aromatase binding	-	0.6120	61.20%
PPAR gamma	+	0.5549	55.49%
Honey bee toxicity	-	0.8770	87.70%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8397	83.97%

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	98.21%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.66%	93.99%
CHEMBL2581	P07339	Cathepsin D	95.87%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.06%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.58%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	86.93%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.95%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.42%	90.00%
CHEMBL238	Q01959	Dopamine transporter	82.37%	95.88%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.29%	93.56%

Plants that contains it

• Rauvolfia serpentina

Cross-Links

• PubChem: 163105773
• LOTUS: LTS0042229
• wikiData: Q105232595