Mamanine

Details

• Internal ID: 9a2b0eb3-6b6d-461f-9db5-1d81ddb5fc1d
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Lupinine-type alkaloids
• IUPAC Name: 6-[(1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl]-1H-pyridin-2-one
• SMILES (Canonical): C1CCN2CC(CC(C2C1)CO)C3=CC=CC(=O)N3
• SMILES (Isomeric): C1CCN2C[C@@H](C[C@@H]([C@H]2C1)CO)C3=CC=CC(=O)N3
• InChI: InChI=1S/C15H22N2O2/c18-10-12-8-11(13-4-3-6-15(19)16-13)9-17-7-2-1-5-14(12)17/h3-4,6,11-12,14,18H,1-2,5,7-10H2,(H,16,19)/t11-,12-,14-/m1/s1
• InChI Key: JAUFYQKXSPWZRV-YRGRVCCFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂N₂O₂
• Molecular Weight: 262.35 g/mol
• Exact Mass: 262.168127949 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 60394-92-5
• 2(1H)-Pyridinone, 6-(octahydro-1-(hydroxymethyl)-2H-quinolizin-3-yl)-, (1alpha,3alpha,9aalpha)-(+)-
• (?)-Mamanine
• 6-[(1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl]-1H-pyridin-2-one
• SCHEMBL563305
• DTXSID90209146
• AKOS040752921

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	+	0.6896	68.96%
Blood Brain Barrier	+	0.8788	87.88%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8923	89.23%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9530	95.30%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.6241	62.41%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6941	69.41%
P-glycoprotein inhibitior	-	0.9447	94.47%
P-glycoprotein substrate	-	0.6497	64.97%
CYP3A4 substrate	+	0.5251	52.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7010	70.10%
CYP3A4 inhibition	-	0.7941	79.41%
CYP2C9 inhibition	-	0.8583	85.83%
CYP2C19 inhibition	-	0.8530	85.30%
CYP2D6 inhibition	-	0.7528	75.28%
CYP1A2 inhibition	-	0.7788	77.88%
CYP2C8 inhibition	-	0.9385	93.85%
CYP inhibitory promiscuity	-	0.5946	59.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6722	67.22%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9766	97.66%
Skin irritation	-	0.7631	76.31%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7026	70.26%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.8920	89.20%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4707	47.07%
Acute Oral Toxicity (c)	III	0.5720	57.20%
Estrogen receptor binding	-	0.7145	71.45%
Androgen receptor binding	-	0.6609	66.09%
Thyroid receptor binding	-	0.7042	70.42%
Glucocorticoid receptor binding	-	0.6822	68.22%
Aromatase binding	-	0.7750	77.50%
PPAR gamma	-	0.5547	55.47%
Honey bee toxicity	-	0.9532	95.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.7616	76.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.37%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.46%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.61%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.28%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.00%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.85%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	91.77%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.20%	93.03%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.98%	93.99%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.26%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.39%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.34%	90.08%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.71%	82.69%
CHEMBL1978	P11511	Cytochrome P450 19A1	83.83%	91.76%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.75%	100.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.35%	88.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.19%	98.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.64%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.18%	95.83%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Malva sylvestris
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora chrysophylla
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 3085182
• NPASS: NPC63684
• LOTUS: LTS0160474
• wikiData: Q83083322