Haplamine

Details

• Internal ID: 9b9f4fb4-d487-4ef8-97de-ff9fa796c0e4
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Pyranoquinolines
• IUPAC Name: 9-methoxy-2,2-dimethyl-6H-pyrano[3,2-c]quinolin-5-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C3=C(C=CC(=C3)OC)NC2=O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C3=C(C=CC(=C3)OC)NC2=O)C
• InChI: InChI=1S/C15H15NO3/c1-15(2)7-6-10-13(19-15)11-8-9(18-3)4-5-12(11)16-14(10)17/h4-8H,1-3H3,(H,16,17)
• InChI Key: IXRKDGGGFFCRIR-UHFFFAOYSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₅NO₃
• Molecular Weight: 257.28 g/mol
• Exact Mass: 257.10519334 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.72
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• MLS000073264
• 52617-31-9
• 9-methoxy-2,2-dimethyl-6H-pyrano[3,2-c]quinolin-5-one
• SMR000001289
• 9-Methoxy-2,2-dimethyl-2,6-dihydro-pyrano[3,2-c]quinolin-5-one
• TNP00205
• Opera_ID_1486
• CBMicro_015460
• Cambridge id 5255761
• Oprea1_154408
• Oprea1_706653
• Oprea1_832596
• SCHEMBL257952
• cid_648601
• CHEMBL1488010
• BDBM36843
• CHEBI:182487
• DTXSID701346933
• HMS2387D11
• HMS3561F11
• 9-methoxy-2,2-dimethyl-6-hydro-2H-pyrano[5,6-c]quinolin-5-one
• STL443725
• 5H-Pyrano[3,2-c]quinolin-5-one, 2,6-dihydro-9-methoxy-2,2-dimethyl-
• AKOS005223971
• CCG-202816
• NCGC00017285-01
• NCGC00017285-02
• NCGC00017285-03
• NCGC00017285-04
• NCGC00017285-04!HAPLAMINE
• NCGC00017285-06
• NCGC00033691-02
• NCGC00033691-03
• BIM-0015490.P001
• BRD-K54293982-001-18-5
• Q63408972
• 9-methoxy-2,2-dimethyl-2H-pyrano[3,2-c]quinolin-5(6H)-one
• N~1~-(sec-butyl)-N~4~-[(2-methyl-1,3-thiazol-4-yl)methyl]piperidine-1,4-dicarboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.6072	60.72%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6658	66.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9120	91.20%
OATP1B3 inhibitior	+	0.9688	96.88%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7404	74.04%
P-glycoprotein inhibitior	-	0.8279	82.79%
P-glycoprotein substrate	-	0.7313	73.13%
CYP3A4 substrate	+	0.5774	57.74%
CYP2C9 substrate	-	0.6070	60.70%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.6651	66.51%
CYP2C19 inhibition	+	0.5584	55.84%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7556	75.56%
CYP inhibitory promiscuity	+	0.5679	56.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.4491	44.91%
Eye corrosion	-	0.9884	98.84%
Eye irritation	+	0.8921	89.21%
Skin irritation	-	0.8533	85.33%
Skin corrosion	-	0.9657	96.57%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3670	36.70%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.6201	62.01%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5517	55.17%
Estrogen receptor binding	+	0.9739	97.39%
Androgen receptor binding	+	0.7160	71.60%
Thyroid receptor binding	+	0.7119	71.19%
Glucocorticoid receptor binding	+	0.8485	84.85%
Aromatase binding	+	0.8999	89.99%
PPAR gamma	+	0.7679	76.79%
Honey bee toxicity	-	0.8339	83.39%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.6841	68.41%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	19952.6 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	7943.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	25118.9 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	2818.4 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	5011.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.86%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.64%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.93%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.78%	85.14%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	91.92%	85.30%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.64%	94.00%
CHEMBL2535	P11166	Glucose transporter	90.82%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.82%	96.09%
CHEMBL1907	P15144	Aminopeptidase N	89.40%	93.31%
CHEMBL4208	P20618	Proteasome component C5	85.85%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	84.92%	98.59%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.83%	96.77%
CHEMBL1951	P21397	Monoamine oxidase A	82.76%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.28%	86.92%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.61%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.39%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.32%	92.62%
CHEMBL2581	P07339	Cathepsin D	81.17%	98.95%

Plants that contains it

• Haplophyllum acutifolium
• Haplophyllum bucharicum
• Haplophyllum villosum
• Swietenia mahagoni
• Vepris bilocularis

Cross-Links

• PubChem: 648601
• NPASS: NPC66083
• ChEMBL: CHEMBL1488010
• LOTUS: LTS0038477
• wikiData: Q63408972