(1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde

Details

• Internal ID: c335c05e-e12f-407d-a656-dd9f8da65152
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: (1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde
• SMILES (Canonical): CC=C1CN2C3CC1C(C2CC4=C3N(C5=C4C=CC=C5OC)C)C=O
• SMILES (Isomeric): C/C=C\1/CN2[C@H]3C[C@H]1[C@H]([C@@H]2CC4=C3N(C5=C4C=CC=C5OC)C)C=O
• InChI: InChI=1S/C21H24N2O2/c1-4-12-10-23-17-9-15-13-6-5-7-19(25-3)21(13)22(2)20(15)18(23)8-14(12)16(17)11-24/h4-7,11,14,16-18H,8-10H2,1-3H3/b12-4-/t14-,16-,17+,18+/m1/s1
• InChI Key: RBNBEKDCSALFTN-JNSISUEASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄N₂O₂
• Molecular Weight: 336.40 g/mol
• Exact Mass: 336.183778013 g/mol
• Topological Polar Surface Area (TPSA): 34.50 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.8526	85.26%
Blood Brain Barrier	+	0.8608	86.08%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7804	78.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8649	86.49%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.7035	70.35%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	+	0.7813	78.13%
P-glycoprotein inhibitior	+	0.5831	58.31%
P-glycoprotein substrate	+	0.6727	67.27%
CYP3A4 substrate	+	0.7185	71.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4559	45.59%
CYP3A4 inhibition	+	0.6213	62.13%
CYP2C9 inhibition	-	0.7320	73.20%
CYP2C19 inhibition	-	0.6451	64.51%
CYP2D6 inhibition	+	0.6768	67.68%
CYP1A2 inhibition	+	0.6812	68.12%
CYP2C8 inhibition	+	0.6488	64.88%
CYP inhibitory promiscuity	+	0.8403	84.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6216	62.16%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9942	99.42%
Skin irritation	-	0.7976	79.76%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.9413	94.13%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5284	52.84%
skin sensitisation	-	0.8719	87.19%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6911	69.11%
Acute Oral Toxicity (c)	III	0.6020	60.20%
Estrogen receptor binding	+	0.6618	66.18%
Androgen receptor binding	+	0.6172	61.72%
Thyroid receptor binding	+	0.6165	61.65%
Glucocorticoid receptor binding	+	0.6243	62.43%
Aromatase binding	-	0.6238	62.38%
PPAR gamma	-	0.5552	55.52%
Honey bee toxicity	-	0.8031	80.31%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9331	93.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.12%	89.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.43%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.38%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.20%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.83%	85.14%
CHEMBL2535	P11166	Glucose transporter	91.71%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.10%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	89.99%	97.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.42%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.69%	89.62%
CHEMBL2056	P21728	Dopamine D1 receptor	88.65%	91.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.94%	97.25%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.29%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.30%	96.00%
CHEMBL217	P14416	Dopamine D2 receptor	85.25%	95.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.79%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.70%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.59%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.04%	91.11%
CHEMBL228	P31645	Serotonin transporter	80.48%	95.51%
CHEMBL1907	P15144	Aminopeptidase N	80.31%	93.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.06%	97.09%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.00%	85.83%

Plants that contains it

• Rauvolfia bahiensis

Cross-Links

• PubChem: 162995542
• LOTUS: LTS0258353
• wikiData: Q105233200