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[(2R,4S,4aR,7aS,7bR)-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-2,4,4a,5,7,7a-hexahydro-1H-cyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

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 ac45d724-df26-43f4-bcf3-6903c7ce06dc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Illudanes and illudins > Melleolides and analogues
IUPAC Name [(2R,4S,4aR,7aS,7bR)-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-2,4,4a,5,7,7a-hexahydro-1H-cyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C24H31ClO6/c1-11-18(15(27)6-16(30-5)20(11)25)22(29)31-17-9-24(4)14-8-23(2,3)7-12(14)21(28)13(10-26)19(17)24/h6,12,14,17,21,26-28H,7-10H2,1-5H3/t12-,14+,17-,21+,24-/m1/s1
InChI Key OMAGQTXDHXASNM-RNNQDMPLSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C24H31ClO6
Molecular Weight 450.90 g/mol
Exact Mass 450.1809164 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 4.40
Atomic LogP (AlogP) 4.01
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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Arnamiol
[(2R,4S,4aR,7aS,7bR)-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-2,4,4a,5,7,7a-hexahydro-1H-cyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
4'-O-Methylmelleolide P
CH 205-J
SCHEMBL12291319
DTXSID80907083
4-Hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-2,4,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

2D Structure

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2D Structure of [(2R,4S,4aR,7aS,7bR)-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-2,4,4a,5,7,7a-hexahydro-1H-cyclobuta[e]inden-2-yl] 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9934 99.34%
Caco-2 - 0.5424 54.24%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.8506 85.06%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8532 85.32%
OATP1B3 inhibitior + 0.7975 79.75%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.7323 73.23%
P-glycoprotein inhibitior - 0.4812 48.12%
P-glycoprotein substrate - 0.6030 60.30%
CYP3A4 substrate + 0.6811 68.11%
CYP2C9 substrate - 0.7986 79.86%
CYP2D6 substrate - 0.8404 84.04%
CYP3A4 inhibition - 0.8007 80.07%
CYP2C9 inhibition - 0.6556 65.56%
CYP2C19 inhibition - 0.6603 66.03%
CYP2D6 inhibition - 0.8955 89.55%
CYP1A2 inhibition - 0.5395 53.95%
CYP2C8 inhibition + 0.6814 68.14%
CYP inhibitory promiscuity + 0.5265 52.65%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9023 90.23%
Carcinogenicity (trinary) Non-required 0.6146 61.46%
Eye corrosion - 0.9882 98.82%
Eye irritation - 0.9114 91.14%
Skin irritation - 0.7009 70.09%
Skin corrosion - 0.9365 93.65%
Ames mutagenesis - 0.6632 66.32%
Human Ether-a-go-go-Related Gene inhibition - 0.3935 39.35%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8272 82.72%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.4764 47.64%
Acute Oral Toxicity (c) III 0.5676 56.76%
Estrogen receptor binding + 0.8245 82.45%
Androgen receptor binding + 0.6883 68.83%
Thyroid receptor binding + 0.6494 64.94%
Glucocorticoid receptor binding + 0.7693 76.93%
Aromatase binding + 0.7522 75.22%
PPAR gamma + 0.6851 68.51%
Honey bee toxicity - 0.7777 77.77%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6255 62.55%
Fish aquatic toxicity + 1.0000 100.00%

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 97.99% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.69% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 95.34% 83.82%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.46% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.00% 94.45%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 87.22% 96.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.95% 95.50%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.40% 89.62%
CHEMBL4208 P20618 Proteasome component C5 84.92% 90.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.37% 92.94%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.21% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.99% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.68% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.51% 91.07%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.11% 92.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.78% 97.09%
CHEMBL2581 P07339 Cathepsin D 82.04% 98.95%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.04% 96.00%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.59% 96.90%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.42% 100.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 188661
LOTUS LTS0159487
wikiData Q82875972