Isoreserpin

Details

• Internal ID: afe1add0-de04-45fe-be4f-1a210b71526c
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl 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): COC1C(CC2CN3CCC4=C(C3CC2C1C(=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
• InChI Key: QEVHRUUCFGRFIF-UHFFFAOYSA-N
• Popularity: 15,569 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

• (-)-Isoreserpine
• Salutensin
• 1263-58-7
• Rauwiloid
• Regroton
• Serpentin
• methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• l -Carpserp
• Diupres
• Butiserpine
• Gamaserpin
• Mepireserpate
• Resercrine
• Rauloycin
• Rauvilid
• Resedin
• Resersana
• Resomine
• Sarpagen
• Serpatone
• Serpresan
• Tenserlix
• Neo-antitersol
• NSC80138
• Rauserpen-alk
• Seda-salurepin
• Serp
• Hydropres ka
• Mio-pressin
• Nembu-serpin
• Seda-recipin
• Rauwiloid+
• Serpasil-esidrex
• Drenusil-R
• Serplex K
• Tendoscen-compr.
• Dypertane compound
• Hygroton-reserpine
• Butiserpazide-50
• Raunormin 'orzan'
• Serpasil apresoline
• Adelphin-esidrex-K
• Serpasil-esidrex K
• methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• Tenserpine 'assia'
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
• Arcum R-S
• Sinesalin composition
• Serpentine 'pharbil'
• Unipres (Salt/Mix)
• Serpasil-esidrex no. 1
• Serpasil-esidrex no. 2
• ChemDiv1_007189
• Demi-Regroton (Salt/Mix)
• Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
• CHEMBL357497
• SCHEMBL5372168
• CHEBI:91839
• component of Diupres (Salt/Mix)
• HMS607G17
• DTXSID30925499
• component of Naquival (Salt/Mix)
• component of Regroton (Salt/Mix)
• QEVHRUUCFGRFIF-UHFFFAOYSA-N
• HMS3269P15
• HMS3369J06
• component of Hydropres (Salt/Mix)
• component of Renese R (Salt/Mix)
• component of Metatensin (Salt/Mix)
• component of Salutensin (Salt/Mix)
• NSC-80138
• NSC169414
• component of Diutensen-R (Salt/Mix)
• AKOS004912845
• component of Butiserpazide (Salt/Mix)
• NSC-169414
• NCGC00015888-03
• NCGC00015888-04
• NCGC00015888-05
• NCGC00142390-01
• NCGC00142390-02
• 3,8-dimethoxy-4-(methoxycarbonyl)-1,2,3,4,5,11,14,14a,4a,5a-decahydrobenzo[3,4 -g]indolo[2,3-a]quinolizin-2-yl 3,4,5-trimethoxybenzoate
• AS-13241
• Methyl reserpate 3,4,5-trimethoxybenzoate
• FT-0674350
• Methyl reserpate 3,4,5-trimethyloxybenzoic acid
• L000827
• Reserpic acid methyl ester 3,4,5-trimethoxybenzoate
• BRD-A71765365-001-01-6
• Q27163633
• Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate #
• 1,2,3,4,4a,5,7,8,13,13b,14,14a-Dodecahydro-2,11-dimethoxy-3-(3,4,5-trimethoxybenzoyloxy)benz[g]indolo[2,3-a]quinolizine-1-carboxylic acid methyl ester
• 20.alpha.-Yohimban-16.beta.-carboxylic acid,17.alpha.-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)
• 3-.beta.,20-.alpha.-Yohimban-16-.beta.-carboxylic acid, 18-.beta.-hydroxy-11,17-.alpha.-dimethoxy-,methyl ester, 3,4,5-trimethoxybenzoate
• 3.beta.,20.alpha.-Yohimban-16.beta.-carboxylic acid, 18.beta.-hydroxy-11,17.alpha.-dimethoxy- methyl ester 3,4,5-trimethoxybenzoate (ester)
• 6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester
• Benz(g)indolo(2,3-a)quinolizine-1-carboxylic acid, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate
• Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate 3,4,5-trimethoxybenzoate (ester)
• Yohimban-16-carboxylic acid,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (16.beta.,17.alpha.,18.beta.,20.alpha.)-

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
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	28183.8 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1893	Q05940	Synaptic vesicular amine transporter	5.26 nM	Ki	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	70794.6 nM; 28183.8 nM	Potency; Potency	via CMAUP; 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

• Alstonia constricta
• Alstonia yunnanensis
• Catharanthus roseus
• Rauvolfia serpentina
• Rauvolfia verticillata
• Rauvolfia vomitoria

Cross-Links

• PubChem: 5052
• NPASS: NPC315634
• ChEMBL: CHEMBL357497
• LOTUS: LTS0210490
• wikiData: Q27163633