Aristololactam

Details

• Internal ID: 60b151b8-8ec2-4ce2-9ac6-7e14f98c6e82
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 14-methoxy-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)NC(=O)C4=CC5=C3OCO5
• SMILES (Isomeric): COC1=CC=CC2=C3C4=C(C=C21)NC(=O)C4=CC5=C3OCO5
• InChI: InChI=1S/C17H11NO4/c1-20-12-4-2-3-8-9(12)5-11-14-10(17(19)18-11)6-13-16(15(8)14)22-7-21-13/h2-6H,7H2,1H3,(H,18,19)
• InChI Key: MXOKGWUJNGEKBH-UHFFFAOYSA-N
• Popularity: 50 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₁NO₄
• Molecular Weight: 293.27 g/mol
• Exact Mass: 293.06880783 g/mol
• Topological Polar Surface Area (TPSA): 56.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Aristolactam I
• 13395-02-3
• Aristololactam I
• Aristolactam
• Aristololactum
• NSC 87406
• CCRIS 1545
• Aristololactam; Aristolactam
• BRN 0307971
• 3G8CFM4T9A
• CHEMBL479127
• NSC-87406
• 8-Methoxybenzo[f]-1,3-benzodioxolo[6,5,4-cd]indol-5(6H)-one
• Benzo(f)-1,3-benzodioxolo(6,5,4-cd)indol-5(6H)-one, 8-methoxy-
• 14-methoxy-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
• 4-27-00-06628 (Beilstein Handbook Reference)
• Benzo[f]-1,3-benzodioxolo[6,5,4-cd]indol-5(6H)-one, 8-methoxy-
• Aristolactam-I
• UNII-3G8CFM4T9A
• DTXSID60158430
• HY-N2013
• NSC87406
• BDBM50306869
• MFCD00797313
• AKOS028111118
• AC-34507
• LS-33655
• MS-24190
• CS-0018333
• FT-0697578
• Q-100130
• 8-methoxy-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-cd]benzo[f]indol-5(6H)-one
• 8-Methoxy-6H-benzo[f][1,3]dioxolo[4'',5'':4,5]benzo[1,2,3-cd]indol-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.8846	88.46%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5644	56.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9471	94.71%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8423	84.23%
P-glycoprotein inhibitior	-	0.7004	70.04%
P-glycoprotein substrate	-	0.6708	67.08%
CYP3A4 substrate	+	0.6400	64.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8485	84.85%
CYP3A4 inhibition	+	0.8468	84.68%
CYP2C9 inhibition	+	0.6855	68.55%
CYP2C19 inhibition	+	0.5082	50.82%
CYP2D6 inhibition	-	0.6677	66.77%
CYP1A2 inhibition	+	0.9155	91.55%
CYP2C8 inhibition	-	0.6524	65.24%
CYP inhibitory promiscuity	+	0.8380	83.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4445	44.45%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.4878	48.78%
Skin irritation	-	0.7774	77.74%
Skin corrosion	-	0.9630	96.30%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4188	41.88%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8286	82.86%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.7397	73.97%
Acute Oral Toxicity (c)	III	0.6021	60.21%
Estrogen receptor binding	+	0.9076	90.76%
Androgen receptor binding	+	0.6604	66.04%
Thyroid receptor binding	+	0.5807	58.07%
Glucocorticoid receptor binding	+	0.8753	87.53%
Aromatase binding	+	0.7100	71.00%
PPAR gamma	+	0.8252	82.52%
Honey bee toxicity	-	0.7530	75.30%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.8105	81.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL301	P24941	Cyclin-dependent kinase 2	1200 nM	IC50	PMID: 20097066

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.75%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.25%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.95%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.93%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.27%	94.80%
CHEMBL2581	P07339	Cathepsin D	94.37%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.35%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.11%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.80%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.16%	92.62%
CHEMBL2535	P11166	Glucose transporter	91.64%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.31%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.51%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.27%	85.14%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.21%	82.67%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	86.02%	80.96%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.98%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	85.04%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.42%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.03%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.72%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.22%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.08%	94.73%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.25%	85.30%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.70%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.61%	96.21%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.65%	85.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.52%	96.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.42%	97.09%

Plants that contains it

• Aristolochia auricularia
• Aristolochia baetica
• Aristolochia brevipes
• Aristolochia chilensis
• Aristolochia contorta
• Aristolochia cucurbitifolia
• Aristolochia debilis
• Aristolochia indica
• Aristolochia kaempferi
• Aristolochia manshuriensis
• Aristolochia orbicularis
• Aristolochia pontica
• Aristolochia zollingeriana
• Asarum heterotropoides
• Asarum sieboldii
• Nerium oleander

Cross-Links

• PubChem: 96710
• NPASS: NPC296742
• ChEMBL: CHEMBL479127
• LOTUS: LTS0173717
• wikiData: Q72443760