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Rescinnamidine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 5259e12b-009e-476a-afb4-bfb65dde5ea1
Taxonomy Alkaloids and derivatives > Yohimbine alkaloids
IUPAC Name methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)propanoyloxy]-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)CCC6=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)CCC6=CC(=C(C(=C6)OC)OC)OC
InChI InChI=1S/C35H44N2O9/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/h8-9,13-14,16,20,24,26,29,31,34,36H,7,10-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1
InChI Key PYYLUPQQQNZLDO-LAFLMMDJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C35H44N2O9
Molecular Weight 636.70 g/mol
Exact Mass 636.30468099 g/mol
Topological Polar Surface Area (TPSA) 118.00 Ų
XlogP 4.30
Atomic LogP (AlogP) 4.49
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 10

Synonyms

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110222-52-1
DTXSID40911545
AKOS040753729
O-[3-(3,4,5-Trimethoxyphenyl)propanoyl]reserpic acid methyl
Methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)propanoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
methyl (1S,2R,3R,4aS,13bR,14aS)-2,11-dimethoxy-3-((3-(3,4,5-trimethoxyphenyl)propanoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-{[3-(3,4,5-trimethoxyphenyl)propanoyl]oxy}yohimban-16-carboxylate
methyl 11,17-dimethoxy-18-{[3-(3,4,5-trimethoxyphenyl)propanoyl]oxy}yohimban-16-carboxylate
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-(1-oxo-3-(3,4,5-trimethoxyphenyl)propoxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)

2D Structure

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2D Structure of Rescinnamidine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8821 88.21%
Caco-2 - 0.7826 78.26%
Blood Brain Barrier + 0.9500 95.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7139 71.39%
OATP2B1 inhibitior - 0.5426 54.26%
OATP1B1 inhibitior - 0.4751 47.51%
OATP1B3 inhibitior - 0.5000 50.00%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.6139 61.39%
BSEP inhibitior + 0.9887 98.87%
P-glycoprotein inhibitior + 0.9210 92.10%
P-glycoprotein substrate + 0.8774 87.74%
CYP3A4 substrate + 0.6936 69.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.4730 47.30%
CYP3A4 inhibition - 0.7970 79.70%
CYP2C9 inhibition - 0.8900 89.00%
CYP2C19 inhibition - 0.8775 87.75%
CYP2D6 inhibition - 0.9305 93.05%
CYP1A2 inhibition + 0.7570 75.70%
CYP2C8 inhibition + 0.7523 75.23%
CYP inhibitory promiscuity - 0.5178 51.78%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5828 58.28%
Eye corrosion - 0.9918 99.18%
Eye irritation - 0.9455 94.55%
Skin irritation - 0.8107 81.07%
Skin corrosion - 0.9565 95.65%
Ames mutagenesis - 0.9000 90.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8932 89.32%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.8750 87.50%
skin sensitisation - 0.9157 91.57%
Respiratory toxicity + 0.9111 91.11%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.8491 84.91%
Acute Oral Toxicity (c) II 0.5410 54.10%
Estrogen receptor binding + 0.8110 81.10%
Androgen receptor binding + 0.8407 84.07%
Thyroid receptor binding + 0.5878 58.78%
Glucocorticoid receptor binding + 0.7917 79.17%
Aromatase binding - 0.5236 52.36%
PPAR gamma + 0.7244 72.44%
Honey bee toxicity - 0.7009 70.09%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5151 51.51%
Fish aquatic toxicity + 0.7655 76.55%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 99.65% 96.09%
CHEMBL4302 P08183 P-glycoprotein 1 99.11% 92.98%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.77% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.32% 91.11%
CHEMBL5747 Q92793 CREB-binding protein 94.79% 95.12%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.11% 99.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.00% 97.09%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 92.99% 95.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.93% 95.56%
CHEMBL255 P29275 Adenosine A2b receptor 92.29% 98.59%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.80% 85.14%
CHEMBL2535 P11166 Glucose transporter 91.19% 98.75%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.28% 94.00%
CHEMBL2581 P07339 Cathepsin D 88.82% 98.95%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 88.78% 89.05%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 88.59% 92.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.56% 95.89%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 88.37% 91.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.23% 86.33%
CHEMBL3820 P35557 Hexokinase type IV 86.76% 91.96%
CHEMBL3437 Q16853 Amine oxidase, copper containing 85.86% 94.00%
CHEMBL4208 P20618 Proteasome component C5 85.36% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.95% 95.89%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 83.94% 90.95%
CHEMBL1744525 P43490 Nicotinamide phosphoribosyltransferase 83.90% 96.25%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.13% 93.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.43% 94.33%
CHEMBL340 P08684 Cytochrome P450 3A4 82.35% 91.19%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 80.91% 89.62%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.70% 97.28%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Rauvolfia serpentina

Cross-Links

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PubChem 184180
NPASS NPC173634
LOTUS LTS0070041
wikiData Q82881692