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(1R,3Z,6R,7Z,9S,11Z,13R,14S,17R,18S)-6,14-dihydroxy-18-(1H-indol-3-ylmethyl)-7,9,15,16-tetramethyl-19-azatricyclo[11.7.0.01,17]icosa-3,7,11,15-tetraene-2,5,20-trione

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 24fa518e-3f21-444a-9c45-dbd88d35c926
Taxonomy Organoheterocyclic compounds > Isoindoles and derivatives > Isoindolines > Isoindolones
IUPAC Name (1R,3Z,6R,7Z,9S,11Z,13R,14S,17R,18S)-6,14-dihydroxy-18-(1H-indol-3-ylmethyl)-7,9,15,16-tetramethyl-19-azatricyclo[11.7.0.01,17]icosa-3,7,11,15-tetraene-2,5,20-trione
SMILES (Canonical) CC1CC=CC2C(C(=C(C3C2(C(=O)C=CC(=O)C(C(=C1)C)O)C(=O)NC3CC4=CNC5=CC=CC=C54)C)C)O
SMILES (Isomeric) C[C@H]/1C/C=C\[C@H]2[C@@H](C(=C([C@@H]3[C@@]2(C(=O)/C=C\C(=O)[C@@H](/C(=C1)/C)O)C(=O)N[C@H]3CC4=CNC5=CC=CC=C54)C)C)O
InChI InChI=1S/C32H36N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-14,16-17,23,25,28-30,33,37-38H,8,15H2,1-4H3,(H,34,39)/b10-7-,13-12-,18-14-/t17-,23-,25-,28-,29+,30+,32+/m0/s1
InChI Key VUEFRYQBOMQOMV-QGODYLGVSA-N
Popularity 79 references in papers

Physical and Chemical Properties

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Molecular Formula C32H36N2O5
Molecular Weight 528.60 g/mol
Exact Mass 528.26242225 g/mol
Topological Polar Surface Area (TPSA) 120.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 3.74
H-Bond Acceptor 5
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3Z,6R,7Z,9S,11Z,13R,14S,17R,18S)-6,14-dihydroxy-18-(1H-indol-3-ylmethyl)-7,9,15,16-tetramethyl-19-azatricyclo[11.7.0.01,17]icosa-3,7,11,15-tetraene-2,5,20-trione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9868 98.68%
Caco-2 - 0.8183 81.83%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Plasma membrane 0.5073 50.73%
OATP2B1 inhibitior - 0.8546 85.46%
OATP1B1 inhibitior + 0.8476 84.76%
OATP1B3 inhibitior + 0.9261 92.61%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9865 98.65%
P-glycoprotein inhibitior + 0.7059 70.59%
P-glycoprotein substrate + 0.6982 69.82%
CYP3A4 substrate + 0.7106 71.06%
CYP2C9 substrate - 0.8000 80.00%
CYP2D6 substrate - 0.8463 84.63%
CYP3A4 inhibition - 0.8115 81.15%
CYP2C9 inhibition - 0.6490 64.90%
CYP2C19 inhibition - 0.7230 72.30%
CYP2D6 inhibition - 0.8501 85.01%
CYP1A2 inhibition - 0.7864 78.64%
CYP2C8 inhibition + 0.6641 66.41%
CYP inhibitory promiscuity + 0.7224 72.24%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4059 40.59%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9600 96.00%
Skin irritation - 0.7774 77.74%
Skin corrosion - 0.9389 93.89%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6554 65.54%
Micronuclear + 0.7700 77.00%
Hepatotoxicity + 0.5625 56.25%
skin sensitisation - 0.8591 85.91%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.7868 78.68%
Acute Oral Toxicity (c) II 0.4829 48.29%
Estrogen receptor binding + 0.7807 78.07%
Androgen receptor binding + 0.6349 63.49%
Thyroid receptor binding + 0.6805 68.05%
Glucocorticoid receptor binding + 0.8233 82.33%
Aromatase binding + 0.5842 58.42%
PPAR gamma + 0.7687 76.87%
Honey bee toxicity - 0.7282 72.82%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9136 91.36%

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 99.33% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.22% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.61% 95.56%
CHEMBL3310 Q96DB2 Histone deacetylase 11 95.18% 88.56%
CHEMBL3192 Q9BY41 Histone deacetylase 8 94.54% 93.99%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.11% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.97% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 93.57% 94.75%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.20% 94.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.95% 92.62%
CHEMBL5103 Q969S8 Histone deacetylase 10 89.29% 90.08%
CHEMBL2535 P11166 Glucose transporter 89.10% 98.75%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.54% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.06% 97.09%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 86.59% 97.64%
CHEMBL4208 P20618 Proteasome component C5 86.29% 90.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.05% 99.23%
CHEMBL255 P29275 Adenosine A2b receptor 85.99% 98.59%
CHEMBL3155 P34969 Serotonin 7 (5-HT7) receptor 84.23% 90.71%
CHEMBL213 P08588 Beta-1 adrenergic receptor 84.06% 95.56%
CHEMBL5805 Q9NR97 Toll-like receptor 8 84.06% 96.25%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 82.33% 96.39%
CHEMBL4530 P00488 Coagulation factor XIII 82.31% 96.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.51% 94.45%

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.
Gymnosporia acuminata

Cross-Links

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PubChem 102093916
NPASS NPC268604
LOTUS LTS0263124
wikiData Q104395164