14-Hydroxy-10-[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: c5fbe975-390d-4608-a5be-ca15b997e1fc
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 14-hydroxy-10-[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): C1OC2=C(O1)C3=C4C=CC=C(C4=CC5=C3C(=C2)C(=O)N5C6C(C(C(C(O6)CO)O)O)O)O
• SMILES (Isomeric): C1OC2=C(O1)C3=C4C=CC=C(C4=CC5=C3C(=C2)C(=O)N5C6C(C(C(C(O6)CO)O)O)O)O
• InChI: InChI=1S/C22H19NO9/c24-6-14-17(26)18(27)19(28)22(32-14)23-11-4-9-8(2-1-3-12(9)25)16-15(11)10(21(23)29)5-13-20(16)31-7-30-13/h1-5,14,17-19,22,24-28H,6-7H2
• InChI Key: NBGDFNYQBMENCR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₉NO₉
• Molecular Weight: 441.40 g/mol
• Exact Mass: 441.10598118 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6427	64.27%
Caco-2	-	0.8308	83.08%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Nucleus	0.5427	54.27%
OATP2B1 inhibitior	-	0.5638	56.38%
OATP1B1 inhibitior	+	0.8900	89.00%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6501	65.01%
P-glycoprotein inhibitior	-	0.5902	59.02%
P-glycoprotein substrate	-	0.7570	75.70%
CYP3A4 substrate	+	0.6371	63.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8498	84.98%
CYP3A4 inhibition	-	0.7993	79.93%
CYP2C9 inhibition	-	0.8873	88.73%
CYP2C19 inhibition	-	0.8645	86.45%
CYP2D6 inhibition	-	0.8408	84.08%
CYP1A2 inhibition	-	0.7364	73.64%
CYP2C8 inhibition	-	0.6474	64.74%
CYP inhibitory promiscuity	-	0.6750	67.50%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8767	87.67%
Skin irritation	-	0.7788	77.88%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.5451	54.51%
skin sensitisation	-	0.8639	86.39%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6487	64.87%
Acute Oral Toxicity (c)	III	0.4840	48.40%
Estrogen receptor binding	+	0.5949	59.49%
Androgen receptor binding	+	0.5622	56.22%
Thyroid receptor binding	-	0.4948	49.48%
Glucocorticoid receptor binding	+	0.6529	65.29%
Aromatase binding	+	0.5851	58.51%
PPAR gamma	+	0.7072	70.72%
Honey bee toxicity	-	0.8151	81.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.6855	68.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.03%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.20%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.97%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.90%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.70%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.99%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.47%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.19%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.13%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.52%	92.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.50%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.27%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.24%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.19%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	85.85%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	85.49%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.27%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.65%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.22%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.90%	86.33%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.23%	98.46%
CHEMBL3384	Q16512	Protein kinase N1	82.22%	80.71%

Plants that contains it

• Aristolochia cucurbitifolia
• Aristolochia foveolata
• Aristolochia indica
• Aristolochia kaempferi
• Aristolochia mollissima
• Aristolochia zollingeriana

Cross-Links

• PubChem: 162999108
• LOTUS: LTS0001013
• wikiData: Q104249875