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(1R,4R,5R,7S,9E,11R,12S,15R,16S)-4,5,12-trihydroxy-16-(1H-indol-3-ylmethyl)-7,13,14-trimethyl-17-azatricyclo[9.7.0.01,15]octadeca-9,13-diene-2,18-dione

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 8e6225c6-c531-4da9-88d9-af161387f3c1
Taxonomy Alkaloids and derivatives > Cytochalasans > Chaetoglobosins
IUPAC Name (1R,4R,5R,7S,9E,11R,12S,15R,16S)-4,5,12-trihydroxy-16-(1H-indol-3-ylmethyl)-7,13,14-trimethyl-17-azatricyclo[9.7.0.01,15]octadeca-9,13-diene-2,18-dione
SMILES (Canonical) CC1CC=CC2C(C(=C(C3C2(C(=O)CC(C(C1)O)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@H]([C@@H](C1)O)O)C(=O)N[C@H]3CC4=CNC5=CC=CC=C54)C)C)O
InChI InChI=1S/C29H36N2O5/c1-15-7-6-9-20-27(35)17(3)16(2)26-22(12-18-14-30-21-10-5-4-8-19(18)21)31-28(36)29(20,26)25(34)13-24(33)23(32)11-15/h4-6,8-10,14-15,20,22-24,26-27,30,32-33,35H,7,11-13H2,1-3H3,(H,31,36)/b9-6+/t15-,20-,22-,23+,24+,26-,27+,29+/m0/s1
InChI Key XJDXKIUXELETKN-DJHNHPSASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H36N2O5
Molecular Weight 492.60 g/mol
Exact Mass 492.26242225 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 2.81
H-Bond Acceptor 5
H-Bond Donor 5
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,4R,5R,7S,9E,11R,12S,15R,16S)-4,5,12-trihydroxy-16-(1H-indol-3-ylmethyl)-7,13,14-trimethyl-17-azatricyclo[9.7.0.01,15]octadeca-9,13-diene-2,18-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9752 97.52%
Caco-2 - 0.7636 76.36%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.4679 46.79%
OATP2B1 inhibitior - 0.8583 85.83%
OATP1B1 inhibitior + 0.8833 88.33%
OATP1B3 inhibitior + 0.9321 93.21%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9583 95.83%
P-glycoprotein inhibitior + 0.5744 57.44%
P-glycoprotein substrate + 0.6705 67.05%
CYP3A4 substrate + 0.6941 69.41%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8246 82.46%
CYP3A4 inhibition - 0.7205 72.05%
CYP2C9 inhibition - 0.8039 80.39%
CYP2C19 inhibition - 0.7957 79.57%
CYP2D6 inhibition - 0.8968 89.68%
CYP1A2 inhibition - 0.8159 81.59%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.6075 60.75%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.4093 40.93%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9805 98.05%
Skin irritation - 0.7639 76.39%
Skin corrosion - 0.9347 93.47%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6570 65.70%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.5608 56.08%
skin sensitisation - 0.8585 85.85%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity - 0.7064 70.64%
Acute Oral Toxicity (c) II 0.3712 37.12%
Estrogen receptor binding + 0.7537 75.37%
Androgen receptor binding + 0.6286 62.86%
Thyroid receptor binding + 0.5490 54.90%
Glucocorticoid receptor binding + 0.7716 77.16%
Aromatase binding + 0.6492 64.92%
PPAR gamma + 0.7272 72.72%
Honey bee toxicity - 0.7118 71.18%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9354 93.54%

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 99.51% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.57% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.13% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.81% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.78% 96.09%
CHEMBL3192 Q9BY41 Histone deacetylase 8 95.29% 93.99%
CHEMBL1937 Q92769 Histone deacetylase 2 95.05% 94.75%
CHEMBL325 Q13547 Histone deacetylase 1 94.40% 95.92%
CHEMBL2996 Q05655 Protein kinase C delta 93.50% 97.79%
CHEMBL3310 Q96DB2 Histone deacetylase 11 92.68% 88.56%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 92.03% 96.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 91.21% 92.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.72% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.65% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.63% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.52% 94.00%
CHEMBL2535 P11166 Glucose transporter 89.18% 98.75%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 88.67% 97.64%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 87.52% 96.39%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.51% 97.25%
CHEMBL3155 P34969 Serotonin 7 (5-HT7) receptor 86.41% 90.71%
CHEMBL4208 P20618 Proteasome component C5 86.24% 90.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.77% 95.50%
CHEMBL213 P08588 Beta-1 adrenergic receptor 85.19% 95.56%
CHEMBL5103 Q969S8 Histone deacetylase 10 85.19% 90.08%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.11% 89.62%
CHEMBL299 P17252 Protein kinase C alpha 83.41% 98.03%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 82.65% 94.62%
CHEMBL3830 Q2M2I8 Adaptor-associated kinase 81.71% 83.10%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.95% 94.45%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.47% 93.03%
CHEMBL255 P29275 Adenosine A2b receptor 80.34% 98.59%

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.
There are no matching plants.

Cross-Links

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PubChem 21588203
LOTUS LTS0058674
wikiData Q105328899