Pubescine

Details

• Internal ID: 1438a5e3-c9aa-4803-8599-508bede0dc04
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1S,15S,16S,20S)-6-methoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate
• SMILES (Canonical): CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=C4C=CC(=C5)OC
• SMILES (Isomeric): C[C@H]1[C@@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=C4C=CC(=C5)OC
• InChI: InChI=1S/C22H26N2O4/c1-12-17-10-24-7-6-15-14-5-4-13(26-2)8-19(14)23-21(15)20(24)9-16(17)18(11-28-12)22(25)27-3/h4-5,8,11-12,16-17,20,23H,6-7,9-10H2,1-3H3/t12-,16-,17-,20-/m0/s1
• InChI Key: KXEMQEGRZWUKJS-RURTYGRKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆N₂O₄
• Molecular Weight: 382.50 g/mol
• Exact Mass: 382.18925731 g/mol
• Topological Polar Surface Area (TPSA): 63.80 Ų
• XlogP: 2.70

Synonyms

• Raubasinine
• Raubasinin
• 482-96-2
• Reserpinine (C22 alkaloid)
• Heterophylline (VAN)
• TP250R6K5B
• NSC15624
• NSC 15624
• NSC-15624
• Methyl (4S,4aS,13bS,14aS)-11-methoxy-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate
• MLS002638438
• Cinchovatine (VAN)
• Reserpinine (Aricine)
• UNII-BUW4ULQ00A
• UNII-TP250R6K5B
• SCHEMBL1654918
• CHEMBL1329821
• BDBM65524
• DTXSID80275719
• 11-METHOXYTETRAHYDROALSTONINE
• NSC 72136
• AKOS003672766
• CCG-103083
• NCGC00160192-01
• Q2145567
• 16,17-Didehydro-10-methoxy-19alpha-methyloxayohimban-16-carboxylic acid
• Oxayohimban-16-carboxylic acid, 16,17-didehydro-10-methoxy-19-methyl-, methyl ester, (19alpha,20alpha)-
• Oxayohimban-16-carboxylic acid, 16,17-didehydro-11-methoxy-19-methyl-, methyl ester, (19.alpha.,20.alpha.)-
• Oxayohimban-16-carboxylic acid, 16,17-didehydro-11-methoxy-19-methyl-, methyl ester, (19alpha,20alpha)-
• Oxayohimban-16-carboxylic acid,17-didehydro-11-methoxy-19-methyl-, methyl ester, (19.alpha.,20.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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	98.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.22%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.33%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	94.42%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.58%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.14%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.72%	95.56%
CHEMBL2535	P11166	Glucose transporter	88.54%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.69%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.64%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	85.27%	95.12%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.90%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.14%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.86%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.36%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.78%	86.92%
CHEMBL340	P08684	Cytochrome P450 3A4	82.58%	91.19%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.12%	90.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.87%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.61%	100.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	81.41%	91.79%
CHEMBL5028	O14672	ADAM10	80.87%	97.50%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.58%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.57%	95.89%

Plants that contains it

• Aspidosperma excelsum
• Holarrhena pubescens
• Ochrosia alyxioides
• Ochrosia balansae
• Rauvolfia serpentina
• Vinca major

Cross-Links

• PubChem: 72313
• LOTUS: LTS0071273
• wikiData: Q2145567