(1S,11S,13R,16S,18R)-11-ethoxy-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.01,16.02,10.04,8]icosa-2,4(8),9,19-tetraene

Details

• Internal ID: c0346377-5395-4911-a9b7-9f65e3104b57
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Tazettine-type amaryllidaceae alkaloids
• IUPAC Name: (1S,11S,13R,16S,18R)-11-ethoxy-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.01,16.02,10.04,8]icosa-2,4(8),9,19-tetraene
• SMILES (Canonical): CCOC1C2=CC3=C(C=C2C45C=CC(CC4N(CC5O1)C)OC)OCO3
• SMILES (Isomeric): CCO[C@@H]1C2=CC3=C(C=C2[C@@]45C=C[C@@H](C[C@@H]4N(C[C@@H]5O1)C)OC)OCO3
• InChI: InChI=1S/C20H25NO5/c1-4-23-19-13-8-15-16(25-11-24-15)9-14(13)20-6-5-12(22-3)7-17(20)21(2)10-18(20)26-19/h5-6,8-9,12,17-19H,4,7,10-11H2,1-3H3/t12-,17-,18-,19-,20-/m0/s1
• InChI Key: KLPOJDWFOJJRDU-CYZGAOKHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.40 g/mol
• Exact Mass: 359.17327290 g/mol
• Topological Polar Surface Area (TPSA): 49.40 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9618	96.18%
Caco-2	+	0.8896	88.96%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4709	47.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9132	91.32%
OATP1B3 inhibitior	+	0.9427	94.27%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8086	80.86%
P-glycoprotein inhibitior	-	0.5636	56.36%
P-glycoprotein substrate	+	0.5858	58.58%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4335	43.35%
CYP3A4 inhibition	-	0.7435	74.35%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.5288	52.88%
CYP2D6 inhibition	+	0.5780	57.80%
CYP1A2 inhibition	-	0.7780	77.80%
CYP2C8 inhibition	-	0.7870	78.70%
CYP inhibitory promiscuity	+	0.6585	65.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5215	52.15%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9795	97.95%
Skin irritation	-	0.8110	81.10%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8956	89.56%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.5784	57.84%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.5869	58.69%
Acute Oral Toxicity (c)	III	0.7412	74.12%
Estrogen receptor binding	+	0.6252	62.52%
Androgen receptor binding	+	0.6895	68.95%
Thyroid receptor binding	+	0.7417	74.17%
Glucocorticoid receptor binding	+	0.6103	61.03%
Aromatase binding	-	0.4868	48.68%
PPAR gamma	+	0.6420	64.20%
Honey bee toxicity	-	0.7372	73.72%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8972	89.72%

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	99.23%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.04%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.68%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.11%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.22%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.65%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.39%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.35%	92.62%
CHEMBL230	P35354	Cyclooxygenase-2	89.57%	89.63%
CHEMBL255	P29275	Adenosine A2b receptor	86.86%	98.59%
CHEMBL2581	P07339	Cathepsin D	86.64%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.72%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.53%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.03%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.56%	93.40%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.61%	89.50%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.39%	82.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.31%	94.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.17%	96.39%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.44%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	80.40%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.37%	89.00%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	80.23%	95.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.04%	100.00%

Plants that contains it

• Angelica japonica var. hirsutiflora
• Anthoceros punctatus
• Cinchona officinalis
• Clausena anisata
• Crinum bulbispermum
• Datura wrightii
• Elaeocarpus angustifolius
• Helichrysum asperum
• Lophopetalum javanum
• Lupinus holosericeus
• Searsia leptodictya

Cross-Links

• PubChem: 15483834
• NPASS: NPC30741
• LOTUS: LTS0147115
• wikiData: Q105142751