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

Details

• Internal ID: 50039034-e8e2-4833-8a80-ffd41dd24dd8
• Taxonomy: Alkaloids and derivatives > Ajmaline-sarpagine alkaloids
• IUPAC Name: (1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2(7),3,5-triene-6,18-diol
• SMILES (Canonical): CC=C1CN2C3CC1C4C2CC5(C3N(C6=C5C=CC=C6O)C)C4O
• SMILES (Isomeric): C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]4[C@@H]2C[C@@]5([C@H]3N(C6=C5C=CC=C6O)C)[C@H]4O
• InChI: InChI=1S/C20H24N2O2/c1-3-10-9-22-13-7-11(10)16-14(22)8-20(19(16)24)12-5-4-6-15(23)17(12)21(2)18(13)20/h3-6,11,13-14,16,18-19,23-24H,7-9H2,1-2H3/b10-3-/t11-,13-,14-,16-,18-,19-,20+/m0/s1
• InChI Key: KNDQTTHAEJUPJU-HZTCUHRNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.183778013 g/mol
• Topological Polar Surface Area (TPSA): 46.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	+	0.7980	79.80%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8978	89.78%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.7927	79.27%
P-glycoprotein inhibitior	-	0.9042	90.42%
P-glycoprotein substrate	+	0.6160	61.60%
CYP3A4 substrate	+	0.6090	60.90%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.5475	54.75%
CYP3A4 inhibition	-	0.8917	89.17%
CYP2C9 inhibition	-	0.8039	80.39%
CYP2C19 inhibition	-	0.6987	69.87%
CYP2D6 inhibition	+	0.5618	56.18%
CYP1A2 inhibition	-	0.6566	65.66%
CYP2C8 inhibition	-	0.6537	65.37%
CYP inhibitory promiscuity	-	0.5946	59.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6343	63.43%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9866	98.66%
Skin irritation	-	0.7693	76.93%
Skin corrosion	-	0.9202	92.02%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6970	69.70%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5235	52.35%
skin sensitisation	-	0.8212	82.12%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.5732	57.32%
Acute Oral Toxicity (c)	III	0.4964	49.64%
Estrogen receptor binding	+	0.5679	56.79%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	+	0.6822	68.22%
Glucocorticoid receptor binding	-	0.6717	67.17%
Aromatase binding	-	0.6490	64.90%
PPAR gamma	-	0.5798	57.98%
Honey bee toxicity	-	0.8906	89.06%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9304	93.04%

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	96.93%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.81%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.61%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.67%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.92%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.72%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.97%	86.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.79%	85.11%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.42%	91.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.50%	100.00%

Plants that contains it

• Rauvolfia media

Cross-Links

• PubChem: 163104750
• LOTUS: LTS0022242
• wikiData: Q105143352