Ajmalinium

Details

• Internal ID: df1f41ab-344a-4da7-8e1d-479a5ed6a3a2
• Taxonomy: Alkaloids and derivatives > Ajmaline-sarpagine alkaloids
• IUPAC Name: (1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8-aza-15-azoniahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol
• SMILES (Canonical): CCC1C2CC3C4C5(CC(C2C5O)[NH+]3C1O)C6=CC=CC=C6N4C
• SMILES (Isomeric): CC[C@H]1[C@@H]2C[C@H]3[C@H]4[C@@]5(C[C@@H](C2[C@H]5O)[NH+]3[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/p+1/t10-,11-,14-,15-,16?,17-,18+,19+,20+/m0/s1
• InChI Key: CJDRUOGAGYHKKD-HEFSZTOGSA-O
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₇N₂O₂+
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.207253108 g/mol
• Topological Polar Surface Area (TPSA): 48.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.14
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• CHEBI:58567
• ajmalan-4-ium-17alpha,21alpha-diol
• Q27125884

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8060	80.60%
Caco-2	+	0.7783	77.83%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5193	51.93%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.8764	87.64%
OATP1B3 inhibitior	+	0.9382	93.82%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6419	64.19%
P-glycoprotein inhibitior	-	0.8669	86.69%
P-glycoprotein substrate	+	0.5375	53.75%
CYP3A4 substrate	+	0.5506	55.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4425	44.25%
CYP3A4 inhibition	-	0.9487	94.87%
CYP2C9 inhibition	-	0.8733	87.33%
CYP2C19 inhibition	-	0.8477	84.77%
CYP2D6 inhibition	+	0.6859	68.59%
CYP1A2 inhibition	-	0.8461	84.61%
CYP2C8 inhibition	-	0.6452	64.52%
CYP inhibitory promiscuity	-	0.6983	69.83%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5982	59.82%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9853	98.53%
Skin irritation	-	0.7846	78.46%
Skin corrosion	-	0.9204	92.04%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6704	67.04%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8790	87.90%
Acute Oral Toxicity (c)	II	0.5040	50.40%
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	-	0.8928	89.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.6656	66.56%

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	97.99%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.28%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	91.61%	90.17%
CHEMBL2581	P07339	Cathepsin D	88.61%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.82%	97.09%
CHEMBL4208	P20618	Proteasome component C5	87.65%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.57%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.88%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.46%	86.33%

Plants that contains it

• Rauvolfia serpentina
• Rauvolfia verticillata
• Rauvolfia vomitoria

Cross-Links

• PubChem: 45266687
• NPASS: NPC265786