(1R,12R,13R,18R)-6-methoxy-3,16,20-trimethyl-11-oxo-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaene-17-carbaldehyde

Details

• Internal ID: f98aa803-e082-484a-92df-6ce56f544034
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: (1R,12R,13R,18R)-6-methoxy-3,16,20-trimethyl-11-oxo-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaene-17-carbaldehyde
• SMILES (Canonical): CC1=C(C2CC3C4=C(C5=C(N4C)C=C(C=C5)OC)C(=O)C(C2CO1)N3C)C=O
• SMILES (Isomeric): CC1=C([C@@H]2C[C@@H]3C4=C(C5=C(N4C)C=C(C=C5)OC)C(=O)[C@@H]([C@@H]2CO1)N3C)C=O
• InChI: InChI=1S/C22H24N2O4/c1-11-15(9-25)14-8-18-21-19(22(26)20(24(18)3)16(14)10-28-11)13-6-5-12(27-4)7-17(13)23(21)2/h5-7,9,14,16,18,20H,8,10H2,1-4H3/t14-,16+,18+,20+/m0/s1
• InChI Key: AFHGOQPKVXJDHG-JYJIFUJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄N₂O₄
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.17360725 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.86
• H-Bond Acceptor: 6
• 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	+	0.9859	98.59%
Caco-2	+	0.6844	68.44%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4808	48.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8729	87.29%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7815	78.15%
P-glycoprotein inhibitior	+	0.7129	71.29%
P-glycoprotein substrate	-	0.5060	50.60%
CYP3A4 substrate	+	0.6698	66.98%
CYP2C9 substrate	+	0.6034	60.34%
CYP2D6 substrate	-	0.7557	75.57%
CYP3A4 inhibition	+	0.6031	60.31%
CYP2C9 inhibition	-	0.7792	77.92%
CYP2C19 inhibition	-	0.6479	64.79%
CYP2D6 inhibition	-	0.7540	75.40%
CYP1A2 inhibition	+	0.6578	65.78%
CYP2C8 inhibition	-	0.6628	66.28%
CYP inhibitory promiscuity	+	0.6362	63.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5319	53.19%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9765	97.65%
Skin irritation	-	0.8100	81.00%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8772	87.72%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5859	58.59%
skin sensitisation	-	0.8801	88.01%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6311	63.11%
Acute Oral Toxicity (c)	III	0.6650	66.50%
Estrogen receptor binding	+	0.7992	79.92%
Androgen receptor binding	+	0.7946	79.46%
Thyroid receptor binding	+	0.5976	59.76%
Glucocorticoid receptor binding	+	0.7960	79.60%
Aromatase binding	-	0.5321	53.21%
PPAR gamma	+	0.5946	59.46%
Honey bee toxicity	-	0.8104	81.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9691	96.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.40%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.94%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.99%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.36%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.65%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.15%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.77%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.49%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.18%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.05%	94.00%
CHEMBL4208	P20618	Proteasome component C5	86.96%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.51%	89.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.27%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.25%	97.09%
CHEMBL1907	P15144	Aminopeptidase N	84.76%	93.31%
CHEMBL2581	P07339	Cathepsin D	84.07%	98.95%
CHEMBL2535	P11166	Glucose transporter	83.63%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.99%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.93%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.32%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.75%	96.00%

Plants that contains it

• Alstonia macrophylla

Cross-Links

• PubChem: 101730882
• LOTUS: LTS0009248
• wikiData: Q104911205