(1S,14R,17R)-4,17-dimethoxy-11-azatetracyclo[9.7.0.01,14.02,7]octadeca-2,4,6,15-tetraen-5-ol

Details

• Internal ID: 9fc9ade2-6287-41a0-b5a4-a33ff792b780
• Taxonomy: Alkaloids and derivatives > Erythrina alkaloids > Homoerythrinane alkaloids
• IUPAC Name: (1S,14R,17R)-4,17-dimethoxy-11-azatetracyclo[9.7.0.01,14.02,7]octadeca-2,4,6,15-tetraen-5-ol
• SMILES (Canonical): COC1CC23C(CCN2CCCC4=CC(=C(C=C34)OC)O)C=C1
• SMILES (Isomeric): CO[C@@H]1C[C@@]23[C@H](CCN2CCCC4=CC(=C(C=C34)OC)O)C=C1
• InChI: InChI=1S/C19H25NO3/c1-22-15-6-5-14-7-9-20-8-3-4-13-10-17(21)18(23-2)11-16(13)19(14,20)12-15/h5-6,10-11,14-15,21H,3-4,7-9,12H2,1-2H3/t14-,15-,19-/m0/s1
• InChI Key: YWEWDVPBCRELRV-DOXZYTNZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.40 g/mol
• Exact Mass: 315.18344366 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	+	0.8910	89.10%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6818	68.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8982	89.82%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	+	0.7422	74.22%
P-glycoprotein inhibitior	-	0.7155	71.55%
P-glycoprotein substrate	-	0.5707	57.07%
CYP3A4 substrate	+	0.6005	60.05%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	+	0.6478	64.78%
CYP3A4 inhibition	-	0.6823	68.23%
CYP2C9 inhibition	-	0.8514	85.14%
CYP2C19 inhibition	-	0.6187	61.87%
CYP2D6 inhibition	+	0.6293	62.93%
CYP1A2 inhibition	-	0.7483	74.83%
CYP2C8 inhibition	-	0.6870	68.70%
CYP inhibitory promiscuity	-	0.7576	75.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5846	58.46%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9643	96.43%
Skin irritation	-	0.7709	77.09%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8354	83.54%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6205	62.05%
skin sensitisation	-	0.8470	84.70%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8747	87.47%
Acute Oral Toxicity (c)	III	0.5696	56.96%
Estrogen receptor binding	+	0.7358	73.58%
Androgen receptor binding	-	0.5763	57.63%
Thyroid receptor binding	+	0.7473	74.73%
Glucocorticoid receptor binding	+	0.7818	78.18%
Aromatase binding	+	0.5262	52.62%
PPAR gamma	-	0.5443	54.43%
Honey bee toxicity	-	0.8824	88.24%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5751	57.51%
Fish aquatic toxicity	+	0.8136	81.36%

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	98.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.29%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	97.07%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.24%	85.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	92.15%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.14%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.62%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.36%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.85%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.91%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.29%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.02%	93.40%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.91%	90.24%
CHEMBL4208	P20618	Proteasome component C5	84.73%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.68%	94.00%
CHEMBL217	P14416	Dopamine D2 receptor	83.75%	95.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.51%	92.62%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.27%	99.18%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.07%	82.67%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.80%	94.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.49%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.35%	93.04%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.84%	82.38%
CHEMBL3438	Q05513	Protein kinase C zeta	80.38%	88.48%

Plants that contains it

• Phelline comosa

Cross-Links

• PubChem: 162904639
• LOTUS: LTS0117608
• wikiData: Q105366496