14-methoxy-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(18),2(6),7,11(19),12,14,16-heptaen-9-one

Details

• Internal ID: bc4f2817-fd05-4e00-8fc2-1ec0530daae1
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 14-methoxy-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(18),2(6),7,11(19),12,14,16-heptaen-9-one
• SMILES (Canonical): COC1=CC=CC2=C3C4=C(C=C21)N(C(=O)C4=CC5=C3OCO5)C6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC1=CC=CC2=C3C4=C(C=C21)N(C(=O)C4=CC5=C3OCO5)[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C23H21NO9/c1-30-13-4-2-3-9-10(13)5-12-16-11(6-14-21(17(9)16)32-8-31-14)22(29)24(12)23-20(28)19(27)18(26)15(7-25)33-23/h2-6,15,18-20,23,25-28H,7-8H2,1H3/t15-,18-,19+,20-,23-/m1/s1
• InChI Key: GIDCUQKCIZAUKW-BSTKLLGTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₁NO₉
• Molecular Weight: 455.40 g/mol
• Exact Mass: 455.12163125 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.49
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7452	74.52%
Caco-2	-	0.7590	75.90%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Nucleus	0.5114	51.14%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.9018	90.18%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6970	69.70%
P-glycoprotein inhibitior	-	0.4941	49.41%
P-glycoprotein substrate	-	0.6458	64.58%
CYP3A4 substrate	+	0.6689	66.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	-	0.6654	66.54%
CYP2C9 inhibition	-	0.7909	79.09%
CYP2C19 inhibition	-	0.7175	71.75%
CYP2D6 inhibition	-	0.7707	77.07%
CYP1A2 inhibition	-	0.7450	74.50%
CYP2C8 inhibition	-	0.5939	59.39%
CYP inhibitory promiscuity	+	0.5823	58.23%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5432	54.32%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.7944	79.44%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7015	70.15%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5399	53.99%
skin sensitisation	-	0.8758	87.58%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5481	54.81%
Acute Oral Toxicity (c)	III	0.6065	60.65%
Estrogen receptor binding	+	0.6245	62.45%
Androgen receptor binding	+	0.5630	56.30%
Thyroid receptor binding	-	0.5394	53.94%
Glucocorticoid receptor binding	+	0.7336	73.36%
Aromatase binding	+	0.5327	53.27%
PPAR gamma	+	0.6989	69.89%
Honey bee toxicity	-	0.7709	77.09%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	-	0.4103	41.03%

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	98.53%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.46%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.98%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.90%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.90%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.84%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.58%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.26%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.57%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.17%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.28%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.37%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.51%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.46%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.02%	96.00%
CHEMBL2535	P11166	Glucose transporter	85.21%	98.75%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	85.11%	92.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.79%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.60%	95.83%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.37%	82.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.63%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.11%	89.62%

Plants that contains it

• Aristolochia indica
• Aristolochia kaempferi
• Aristolochia mollissima
• Aristolochia pubescens
• Aristolochia zollingeriana

Cross-Links

• PubChem: 10411690
• LOTUS: LTS0000319
• wikiData: Q105008879