Aristolactam AII

Details

• Internal ID: 303baf5a-3d90-4fd9-8c4d-1ee23165e8ce
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 14-hydroxy-15-methoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• SMILES (Canonical): COC1=C(C=C2C3=C1C4=CC=CC=C4C=C3NC2=O)O
• SMILES (Isomeric): COC1=C(C=C2C3=C1C4=CC=CC=C4C=C3NC2=O)O
• InChI: InChI=1S/C16H11NO3/c1-20-15-12(18)7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15/h2-7,18H,1H3,(H,17,19)
• InChI Key: ZEKAIRFOYPDZNC-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₁NO₃
• Molecular Weight: 265.26 g/mol
• Exact Mass: 265.07389321 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 53948-07-5
• Aristolactam-aii
• Aristolactam A II
• CCRIS 2996
• Dibenz(cd,f)indol-4(5H)-one, 2-hydroxy-1-methoxy-
• Dibenz[cd,f]indol-4(5H)-one, 2-hydroxy-1-methoxy-
• Aristololactam A II; NSC 615450
• 14-hydroxy-15-methoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• AristolactamAII
• aristololactam A II
• NSC615450
• CHEMBL390368
• DTXSID50202234
• HY-N2891
• AKOS028108588
• NSC-615450
• CS-0023475
• B0005-476528
• 14-hydroxy-15-methoxy-10-azatetracyclo[7.6.1.0?,?.0??,??]hexadeca-1(16),2(7),3,5,8,12,14-heptaen-11-one
• 14-hydroxy-15-methoxy-10-azatetracyclo[7.6.1.0^{2,7.0^{12,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.7401	74.01%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6413	64.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9001	90.01%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8421	84.21%
P-glycoprotein substrate	-	0.9088	90.88%
CYP3A4 substrate	+	0.5823	58.23%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	-	0.6320	63.20%
CYP2C9 inhibition	-	0.7655	76.55%
CYP2C19 inhibition	-	0.8452	84.52%
CYP2D6 inhibition	-	0.8646	86.46%
CYP1A2 inhibition	+	0.9453	94.53%
CYP2C8 inhibition	-	0.6793	67.93%
CYP inhibitory promiscuity	+	0.5998	59.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4150	41.50%
Eye corrosion	-	0.9935	99.35%
Eye irritation	+	0.5317	53.17%
Skin irritation	-	0.8024	80.24%
Skin corrosion	-	0.9748	97.48%
Ames mutagenesis	+	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7194	71.94%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.6053	60.53%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6828	68.28%
Acute Oral Toxicity (c)	III	0.4583	45.83%
Estrogen receptor binding	+	0.7760	77.60%
Androgen receptor binding	+	0.6940	69.40%
Thyroid receptor binding	+	0.5303	53.03%
Glucocorticoid receptor binding	+	0.9247	92.47%
Aromatase binding	+	0.8307	83.07%
PPAR gamma	+	0.8424	84.24%
Honey bee toxicity	-	0.9003	90.03%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.7317	73.17%

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	99.69%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	95.50%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.71%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.65%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.19%	98.95%
CHEMBL2535	P11166	Glucose transporter	92.41%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.85%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.85%	99.23%
CHEMBL4208	P20618	Proteasome component C5	88.86%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.77%	94.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.69%	93.03%
CHEMBL1907	P15144	Aminopeptidase N	85.83%	93.31%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.27%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.49%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.22%	96.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.78%	96.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.44%	93.99%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.70%	80.78%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.49%	94.08%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.45%	82.69%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	80.18%	81.14%

Plants that contains it

• Annona cacans
• Annona squamosa
• Aristolochia constricta
• Aristolochia foveolata
• Aristolochia indica
• Aristolochia kaempferi
• Aristolochia liukiuensis
• Aristolochia manshuriensis
• Aristolochia mollissima
• Artemisia sericea
• Asarum heterotropoides
• Asarum sieboldii
• Fissistigma balansae
• Fissistigma glaucescens
• Fissistigma oldhamii
• Goniothalamus cheliensis
• Goniothalamus griffithii
• Goniothalamus sesquipedalis
• Goniothalamus tapis
• Houttuynia cordata
• Monocyclanthus vignei
• Mortonia palmeri
• Piper kadsura
• Piper sarmentosum
• Saururus chinensis
• Uvaria littoralis

Cross-Links

• PubChem: 148657
• NPASS: NPC119579
• LOTUS: LTS0239943
• wikiData: Q72443744