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methyl (1R,14R,15R,18S,19R,20S)-14-[(2S,3R,12bS)-2-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-hydroxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-9-yl]-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

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 952d1fc9-caad-4f59-a899-d0a865ddd6bd
Taxonomy Alkaloids and derivatives > Yohimbine alkaloids
IUPAC Name methyl (1R,14R,15R,18S,19R,20S)-14-[(2S,3R,12bS)-2-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-hydroxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-9-yl]-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
SMILES (Canonical) CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=C3C(=C(C=C4)C5C6CCC(C(C6CC7N5CCC8=C7NC9=CC=CC=C89)C(=O)OC)O)O
SMILES (Isomeric) CC[C@H]1CN2CCC3=C([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=C3C(=C(C=C4)[C@H]5[C@@H]6CC[C@@H]([C@@H]([C@H]6C[C@H]7N5CCC8=C7NC9=CC=CC=C89)C(=O)OC)O)O
InChI InChI=1S/C43H52N4O7/c1-5-22-20-46-16-14-26-36-32(45-39(26)33(46)18-28(22)30(21-52-2)42(50)53-3)12-10-27(41(36)49)40-25-11-13-35(48)37(43(51)54-4)29(25)19-34-38-24(15-17-47(34)40)23-8-6-7-9-31(23)44-38/h6-10,12,21-22,25,28-29,33-35,37,40,44-45,48-49H,5,11,13-20H2,1-4H3/b30-21+/t22-,25+,28-,29-,33-,34+,35-,37+,40+/m0/s1
InChI Key VCDQJQMZNBIPGU-AQULUYISSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C43H52N4O7
Molecular Weight 736.90 g/mol
Exact Mass 736.38360001 g/mol
Topological Polar Surface Area (TPSA) 140.00 Ų
XlogP 5.60
Atomic LogP (AlogP) 6.22
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1R,14R,15R,18S,19R,20S)-14-[(2S,3R,12bS)-2-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-hydroxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-9-yl]-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9653 96.53%
Caco-2 - 0.8394 83.94%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7374 73.74%
OATP2B1 inhibitior + 0.5748 57.48%
OATP1B1 inhibitior + 0.8412 84.12%
OATP1B3 inhibitior + 0.8731 87.31%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8811 88.11%
BSEP inhibitior + 0.9759 97.59%
P-glycoprotein inhibitior + 0.7986 79.86%
P-glycoprotein substrate + 0.8842 88.42%
CYP3A4 substrate + 0.7691 76.91%
CYP2C9 substrate + 0.5681 56.81%
CYP2D6 substrate - 0.7616 76.16%
CYP3A4 inhibition - 0.8841 88.41%
CYP2C9 inhibition - 0.8294 82.94%
CYP2C19 inhibition - 0.8869 88.69%
CYP2D6 inhibition - 0.8652 86.52%
CYP1A2 inhibition - 0.7995 79.95%
CYP2C8 inhibition + 0.8027 80.27%
CYP inhibitory promiscuity - 0.7702 77.02%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5689 56.89%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9241 92.41%
Skin irritation - 0.7766 77.66%
Skin corrosion - 0.9385 93.85%
Ames mutagenesis + 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7711 77.11%
Micronuclear + 0.6700 67.00%
Hepatotoxicity - 0.6375 63.75%
skin sensitisation - 0.8787 87.87%
Respiratory toxicity + 0.9111 91.11%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.6177 61.77%
Acute Oral Toxicity (c) III 0.6684 66.84%
Estrogen receptor binding + 0.8280 82.80%
Androgen receptor binding + 0.7951 79.51%
Thyroid receptor binding + 0.5484 54.84%
Glucocorticoid receptor binding + 0.7361 73.61%
Aromatase binding + 0.5958 59.58%
PPAR gamma + 0.7060 70.60%
Honey bee toxicity - 0.7026 70.26%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9523 95.23%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.75% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.42% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 99.21% 94.45%
CHEMBL2581 P07339 Cathepsin D 96.80% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.40% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.25% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.85% 97.09%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 92.18% 91.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.34% 89.00%
CHEMBL2535 P11166 Glucose transporter 90.79% 98.75%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 90.47% 91.79%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 90.26% 97.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.51% 99.23%
CHEMBL228 P31645 Serotonin transporter 87.99% 95.51%
CHEMBL5028 O14672 ADAM10 86.52% 97.50%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.78% 89.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.76% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.76% 95.89%
CHEMBL217 P14416 Dopamine D2 receptor 82.69% 95.62%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.45% 94.33%
CHEMBL213 P08588 Beta-1 adrenergic receptor 81.90% 95.56%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.57% 100.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.76% 93.03%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 80.49% 96.47%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.21% 100.00%

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.
Uncaria callophylla

Cross-Links

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PubChem 101615144
LOTUS LTS0197199
wikiData Q104401736