(+)-Reserpine

Details

• Internal ID: 4044f55d-44aa-473a-a9f2-2a2c45e13b50
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1S,15R,17S,18S,19R,20R)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• SMILES (Canonical): COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
• SMILES (Isomeric): CO[C@@H]1[C@H](C[C@H]2CN3CCC4=C([C@@H]3C[C@H]2[C@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
• InChI: InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m0/s1
• InChI Key: QEVHRUUCFGRFIF-KWTXYEQSSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀N₂O₉
• Molecular Weight: 608.70 g/mol
• Exact Mass: 608.27338086 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 4.00

Synonyms

• (+)-Reserpine
• CHEMBL1396912
• NCGC00016222-01

2D Structure

ADMET Properties (via admetSAR 2)

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

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	6309.6 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	15848.93 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4331	P68871	Hemoglobin beta chain	15848.9 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	10000 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	1412.5 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	17782.8 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	10000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	98.78%	92.98%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.18%	91.11%
CHEMBL2535	P11166	Glucose transporter	96.14%	98.75%
CHEMBL5747	Q92793	CREB-binding protein	95.03%	95.12%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	93.89%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.55%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.39%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.35%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.09%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL4208	P20618	Proteasome component C5	89.55%	90.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	88.36%	90.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.12%	93.40%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	86.00%	97.03%
CHEMBL340	P08684	Cytochrome P450 3A4	85.28%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.67%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.86%	95.89%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.50%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.88%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.73%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.70%	95.89%
CHEMBL1907	P15144	Aminopeptidase N	80.18%	93.31%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.13%	97.28%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.04%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.01%	82.38%

Plants that contains it

• Hypericum perforatum
• Rauvolfia serpentina

Cross-Links

• PubChem: 6604180
• NPASS: NPC100734
• ChEMBL: CHEMBL1396912