Mesembrine

Details

• Internal ID: b005f3f1-f5cd-40c2-acd2-a9e5470182c5
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one
• SMILES (Canonical): CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
• SMILES (Isomeric): CN1CC[C@]2([C@@H]1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
• InChI: InChI=1S/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m0/s1
• InChI Key: DAHIQPJTGIHDGO-IRXDYDNUSA-N
• Popularity: 43 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.40 g/mol
• Exact Mass: 289.16779360 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• (-)-Mesembrine
• 24880-43-1
• Mesembranone
• Mesembrin
• (-)-Mesembranone
• DL-Mesembrine
• Mesembrine [MI]
• (+/-)-Mesembrine
• Mesembrine, (-)-
• (+/-)-Mesembranone
• Mesembrine, (+/-)-
• Mesembrine (+/-)-form [MI]
• 6023-73-0
• 86E2ZU4ETY
• (3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one
• CHEBI:6778
• 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, cis-
• 423182RCI5
• 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aR,7aR)-rel-
• 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aS,7aS)-
• 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3as-cis)-
• 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, cis-(+/-)-
• AC1Q4FEO
• 4alpha,9alpha-Mesembrine
• UNII-86E2ZU4ETY
• AC1L97PM
• 4.alpha.,9.alpha.-Mesembrine
• UNII-423182RCI5
• SureCN225652
• SCHEMBL225652
• CHEMBL2008762
• DTXSID50947774
• DAHIQPJTGIHDGO-IRXDYDNUSA-N
• AKOS040748905
• NCI60_034735
• HY-117526
• CS-0066385
• C09224
• J-015715
• (3aS*,7aS*)-3a-(3,4-dimethoxyphenyl) 1-methyloctahydro-6H-indol-6-one
• (3aS*,7aS*)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-6H-indol-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.9007	90.07%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7615	76.15%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.9480	94.80%
OATP1B3 inhibitior	+	0.9443	94.43%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.5588	55.88%
P-glycoprotein inhibitior	-	0.8459	84.59%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6140	61.40%
CYP2C9 substrate	-	0.6518	65.18%
CYP2D6 substrate	+	0.7417	74.17%
CYP3A4 inhibition	+	0.7644	76.44%
CYP2C9 inhibition	-	0.7972	79.72%
CYP2C19 inhibition	-	0.7008	70.08%
CYP2D6 inhibition	-	0.5145	51.45%
CYP1A2 inhibition	-	0.7683	76.83%
CYP2C8 inhibition	-	0.9508	95.08%
CYP inhibitory promiscuity	-	0.7932	79.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5893	58.93%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9539	95.39%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8603	86.03%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.6051	60.51%
skin sensitisation	-	0.8806	88.06%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6906	69.06%
Acute Oral Toxicity (c)	III	0.4746	47.46%
Estrogen receptor binding	-	0.7038	70.38%
Androgen receptor binding	+	0.6860	68.60%
Thyroid receptor binding	-	0.5585	55.85%
Glucocorticoid receptor binding	-	0.5446	54.46%
Aromatase binding	-	0.5729	57.29%
PPAR gamma	-	0.5861	58.61%
Honey bee toxicity	-	0.8112	81.12%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9211	92.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.45%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.58%	85.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.50%	93.99%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.61%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.96%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.86%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.74%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.49%	90.71%
CHEMBL2535	P11166	Glucose transporter	84.34%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.18%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.98%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.92%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.86%	97.14%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.62%	98.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.58%	91.03%
CHEMBL2056	P21728	Dopamine D1 receptor	82.01%	91.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.95%	91.07%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.60%	93.04%
CHEMBL4208	P20618	Proteasome component C5	81.59%	90.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.51%	95.53%
CHEMBL233	P35372	Mu opioid receptor	81.51%	97.93%
CHEMBL1937	Q92769	Histone deacetylase 2	81.12%	94.75%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.81%	92.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.68%	89.50%
CHEMBL217	P14416	Dopamine D2 receptor	80.17%	95.62%

Plants that contains it

• Mesembryanthemum ladismithiense
• Mesembryanthemum tortuosum

Cross-Links

• PubChem: 394162
• LOTUS: LTS0078755
• wikiData: Q56450441