Rescinnamine

Details

• Internal ID: 0dd2dc00-93c4-4f4b-a08a-2d72cdc97d44
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]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)C=CC6=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)/C=C/C6=CC(=C(C(=C6)OC)OC)OC
• InChI: InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
• InChI Key: SZLZWPPUNLXJEA-QEGASFHISA-N
• Popularity: 275 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₂N₂O₉
• Molecular Weight: 634.70 g/mol
• Exact Mass: 634.28903092 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• Rescinnamin
• 24815-24-5
• Cinnaloid
• Rescisan
• Resealoid
• Scinnamina
• Moderil
• Cartric
• Apoterin
• Anaprel
• Reserpinine
• Cinnasil
• Paresinan
• Raurescin
• Apolon
• Rozex
• Normorescina
• Cinamine
• Cinatabs
• Raupyrol
• Raurescine
• Recinnamine
• Recitensina
• Rescaloid
• Rescamin
• Rescidan
• Rescinpal
• Rescitens
• Reserpinene
• Reskinnamin
• Tenamine
• Rescin
• Resipal
• Tuareg
• Tsuruselpi S
• Methyl trimethoxycinnamoylreserpate
• Reserpinine (C35 alkaloid)
• Reserpinine (VAN)
• Rescinamina
• Rescinnamina
• Rescinnamine (VAN)
• Rescinnaminum
• Rescinnamina [DCIT]
• Apoterin S
• Rescinamina [INN-Spanish]
• Rescinnaminum [INN-Latin]
• Resepinine (C35 alkaloid)
• Reserpinin
• 3,4,5-Trimethoxycinnamoyl methyl reserpate
• Trimethoxycinnamoyl methyl reserpate
• Rescinnamine [BAN:INN:JAN]
• Trimethoxy cinnamoyl reserpate de methyl
• CCRIS 4711
• Tsuruselpi S (TN)
• 3,4,5-Trimethylcinnamoyl methyl reserpate
• HSDB 2176
• 3,4,5-Trimethylcinnamic acid, ester with methyl reserpate
• NSC15628
• EINECS 246-471-8
• Rescinnamine (JAN/INN)
• NSC 15628
• NSC-15628
• 3,4,5-Trimethoxycinnamic acid, methyl reserpate
• Trimethoxy cinnamoyl reserpate de methyl [French]
• UNII-Q6W1F7DJ2D
• Methyl 18-O-(3,4,5-trimethoxycinnamoyl)reserpate
• BRN 0075328
• Q6W1F7DJ2D
• Methyl reserpate 3,4,5-trimethoxycinnamic acid ester
• AI3-52763
• DTXSID3023554
• CHEBI:28572
• Rescinnamine [INN:BAN:JAN:NF]
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
• Anapral
• 11,17alpha-Dimethoxy-18beta-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylic acid methyl ester
• 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester), (E)-
• 4-25-00-01323 (Beilstein Handbook Reference)
• methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• Methyl 1alpha,2beta,3alpha,4,4aalpha,5,7,8,13,13bbeta,14,14aalpha-dodecahydro-2alpha,11-dimethoxy-3beta-(3,4,5-trimethoxycinnamoyloxy)benz(g)indolo(2,3-a)quinolizine-1beta-carboxylate
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-oxy)-, methyl ester, (3beta,16beta,17alpha,18beta(E),20alpha)-
• Reserpic acid methyl ester 3,4,5-trimethoxycinnamate
• 3,4,5-trimethoxycinnamic acid ester of methyl reserpate
• O-(3,4,5-Trimethoxy-trans-cinnamoyl) methyl reserpate
• Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate
• 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
• 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
• NCGC00016787-01
• Cinnasil (TN)
• methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-({(2E)-3-[3,4,5-tris(methyloxy)phenyl]prop-2-enoyl}oxy)yohimban-16-carboxylate
• Prestwick_558
• Anaprel (TN)
• Moderil (TN)
• CAS-24815-24-5
• Prestwick2_000568
• Prestwick3_000568
• RESCINNAMINE [MI]
• RESCINNAMINE [INN]
• RESCINNAMINE [JAN]
• D0G8NJ
• RESCINNAMINE [HSDB]
• CHEMBL1668
• RESCINNAMINE [VANDF]
• BSPBio_000356
• RESCINNAMINE [MART.]
• MLS002153878
• RESCINNAMINE [WHO-DD]
• SCHEMBL181966
• Rescinnamine [INN:BAN:JAN]
• BPBio1_000392
• GTPL7098
• MEGxp0_001952
• ACon1_002115
• CHEBI:92923
• DTXCID001079620
• HMS1569B18
• HMS2096B18
• HMS2234E08
• RESCINNAMINE [ORANGE BOOK]
• 3.beta.,20.alpha.-Yohimban-16.beta.-carboxylic acid, 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
• HY-A0220
• Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate
• Tox21_110611
• AKOS040744469
• LS-1060
• 3,5-Trimethoxycinnamoyl methyl reserpate
• NCGC00179585-03
• NCGC00179585-04
• SMR001233232
• NP-011016
• 3,5-Trimethoxycinnamic acid, methyl reserpate
• C06540
• D00198
• EN300-19731914
• METHYL 3,4,5-TRIMETHOXYCINNAMOYL RESERPATE
• Q409978
• BRD-K52930707-001-02-2
• BRD-K52930707-001-04-8
• (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-11,17-DIMETHOXY-18-(((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPEN-1-YL)OXY)-YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER
• 11,17-Dimethoxy-18-[[1-oxo-3-3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-3,20-yohimban-16-carboxylic acid methyl ester
• 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-,methyl ester, 3,4,5-trimethoxycinnamate (ester)
• 3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
• Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate
• methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
• methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• methyl 11,17alpha-dimethoxy-18beta-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3beta,20alpha-yohimban-16beta-carboxylate
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-(((2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3b,16b,17a,18b,20a)-
• Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
• Yohimban-16-carboxylic acid,17-dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
• Yohimban-16-carboxylicacid,11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]oxy]-,methyl ester, (3b,16b,17a,18b,20a)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9408	94.08%
Caco-2	-	0.7863	78.63%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7187	71.87%
OATP2B1 inhibitior	-	0.5331	53.31%
OATP1B1 inhibitior	-	0.4426	44.26%
OATP1B3 inhibitior	-	0.5000	50.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6389	63.89%
BSEP inhibitior	+	0.9937	99.37%
P-glycoprotein inhibitior	+	0.9511	95.11%
P-glycoprotein substrate	+	0.7967	79.67%
CYP3A4 substrate	+	0.6701	67.01%
CYP2C9 substrate	-	0.8263	82.63%
CYP2D6 substrate	-	0.7264	72.64%
CYP3A4 inhibition	-	0.8203	82.03%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9144	91.44%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.7362	73.62%
CYP inhibitory promiscuity	-	0.7162	71.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5265	52.65%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7906	79.06%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9403	94.03%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8945	89.45%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8246	82.46%
Acute Oral Toxicity (c)	III	0.8016	80.16%
Estrogen receptor binding	+	0.8413	84.13%
Androgen receptor binding	+	0.8579	85.79%
Thyroid receptor binding	+	0.6167	61.67%
Glucocorticoid receptor binding	+	0.8336	83.36%
Aromatase binding	+	0.5642	56.42%
PPAR gamma	+	0.7375	73.75%
Honey bee toxicity	-	0.6949	69.49%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8821	88.21%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.54%	96.09%
CHEMBL4302	P08183	P-glycoprotein 1	98.48%	92.98%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.07%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.79%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.34%	97.09%
CHEMBL5747	Q92793	CREB-binding protein	91.11%	95.12%
CHEMBL2535	P11166	Glucose transporter	90.70%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.60%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.25%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.81%	94.08%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.83%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.61%	89.62%
CHEMBL255	P29275	Adenosine A2b receptor	87.41%	98.59%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.81%	89.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	84.78%	91.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.71%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.25%	95.89%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.65%	90.95%
CHEMBL228	P31645	Serotonin transporter	83.46%	95.51%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.11%	97.28%
CHEMBL4208	P20618	Proteasome component C5	83.04%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.93%	91.19%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.86%	100.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.76%	96.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.21%	94.33%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.20%	92.38%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.13%	93.40%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.28%	91.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.09%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.04%	93.00%

Plants that contains it

• Rauvolfia mannii
• Rauvolfia serpentina
• Rauvolfia volkensii

Cross-Links

• PubChem: 5280954
• NPASS: NPC284685
• ChEMBL: CHEMBL1668
• LOTUS: LTS0122419
• wikiData: Q409978