Piperolactam A

Details

• Internal ID: f7c2c05f-ecae-4646-8016-ce7d732bc407
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 15-hydroxy-14-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(C2=C3C(=C1)C(=O)NC3=CC4=CC=CC=C42)O
• SMILES (Isomeric): COC1=C(C2=C3C(=C1)C(=O)NC3=CC4=CC=CC=C42)O
• InChI: InChI=1S/C16H11NO3/c1-20-12-7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15(12)18/h2-7,18H,1H3,(H,17,19)
• InChI Key: KBGNBPGXVKPRQI-UHFFFAOYSA-N
• Popularity: 19 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

• Aristolactam FI
• 112501-42-5
• Aristolactam F1
• 1-Hydroxy-2-methoxydibenz(cd,f)indol-4(5H)-one
• Dibenz[cd,f]indol-4(5H)-one, 1-hydroxy-2-methoxy-
• 15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• Dibenz(cd,f)indol-4(5H)-one, 1-hydroxy-2-methoxy-
• 1-Hydroxy-2-methoxydibenz[cd,f]indol-4(5H)-one; Aristololactam FI
• 1-Hydroxy-2-methoxy-Dibenz(cd,f)indol-4(5H)-one
• 1-Hydroxy-2-methoxy-Dibenz[cd,f]indol-4(5H)-one
• CHEMBL387864
• DTXSID90150083
• CHEBI:174488
• HY-N2894
• AKOS028108734
• NCGC00385457-01
• CS-0023479
• 1-Hydroxy-2-methoxydibenz[cd,f]indol-4(5H)-one, 9CI
• B0005-189391
• NCGC00385457-01_C16H11NO3_1-Hydroxy-2-methoxydibenzo[cd,f]indol-4(5H)-one
• 15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.7953	79.53%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6413	64.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8656	86.56%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6002	60.02%
P-glycoprotein inhibitior	-	0.7734	77.34%
P-glycoprotein substrate	-	0.7421	74.21%
CYP3A4 substrate	+	0.5930	59.30%
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	+	0.4861	48.61%
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	+	0.6520	65.20%
Skin irritation	-	0.8024	80.24%
Skin corrosion	-	0.9748	97.48%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7527	75.27%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7177	71.77%
Acute Oral Toxicity (c)	III	0.4583	45.83%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	+	0.7116	71.16%
Thyroid receptor binding	+	0.6292	62.92%
Glucocorticoid receptor binding	+	0.9509	95.09%
Aromatase binding	+	0.8429	84.29%
PPAR gamma	+	0.7981	79.81%
Honey bee toxicity	-	0.8772	87.72%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5851	58.51%
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	99.44%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	95.01%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.00%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.82%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.02%	98.95%
CHEMBL2535	P11166	Glucose transporter	91.21%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.69%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.07%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.88%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.40%	99.23%
CHEMBL1255126	O15151	Protein Mdm4	86.59%	90.20%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.32%	93.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.54%	92.62%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.27%	96.67%
CHEMBL3401	O75469	Pregnane X receptor	83.41%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.85%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.84%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.25%	99.15%

Plants that contains it

• Aristolochia cucurbitifolia
• Aristolochia kaempferi
• Artemisia sericea
• Asplenium adiantum-nigrum
• Distemonanthus benthamianus
• Fissistigma balansae
• Fissistigma glaucescens
• Fissistigma oldhamii
• Goniothalamus tapis
• Houttuynia cordata
• Mortonia palmeri
• Piper argyrophyllum
• Piper attenuatum
• Piper kadsura
• Piper kwashoense
• Piper longum
• Piper sanctum
• Piper sarmentosum

Cross-Links

• PubChem: 3081016
• NPASS: NPC311936
• ChEMBL: CHEMBL387864
• LOTUS: LTS0137147
• wikiData: Q72443757