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(2R,3S,4aS,7R,8R,8aS)-2,3,4'-trihydroxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-7,8-dihydro-3H-furo[2,3-e]isoindole]-6'-one

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 588d2297-9280-4327-bdc2-ecd4b84c0e34
Taxonomy Organoheterocyclic compounds > Isoindoles and derivatives > Isoindolines > Isoindolones
IUPAC Name (2R,3S,4aS,7R,8R,8aS)-2,3,4'-trihydroxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-7,8-dihydro-3H-furo[2,3-e]isoindole]-6'-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C23H31NO5/c1-11-5-6-17-21(2,3)19(27)16(26)9-22(17,4)23(11)8-13-15(25)7-12-14(18(13)29-23)10-24-20(12)28/h7,11,16-17,19,25-27H,5-6,8-10H2,1-4H3,(H,24,28)/t11-,16-,17+,19-,22+,23-/m1/s1
InChI Key RUBLIKRGQGISNL-DXORJMCXSA-N
Popularity 7 references in papers

Physical and Chemical Properties

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Molecular Formula C23H31NO5
Molecular Weight 401.50 g/mol
Exact Mass 401.22022309 g/mol
Topological Polar Surface Area (TPSA) 99.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 2.51
H-Bond Acceptor 5
H-Bond Donor 4
Rotatable Bonds 0

Synonyms

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159096-43-2
Antibiotic F 1839A
CHEMBL3104974
DTXSID101346959
AKOS040735671
F1839-A
NCGC00347551-02
NCGC00347551-02_C23H31NO5_(2R,2'R,4a'S,6'S,7'R,8a'S)-4,6',7'-Trihydroxy-2',5',5',8a'-tetramethyl-3',4',4a',5',6',7,7',8,8',8a'-decahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-6(3H)-one

2D Structure

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2D Structure of (2R,3S,4aS,7R,8R,8aS)-2,3,4'-trihydroxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-7,8-dihydro-3H-furo[2,3-e]isoindole]-6'-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9807 98.07%
Caco-2 - 0.5794 57.94%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability + 0.6000 60.00%
Subcellular localzation Mitochondria 0.7035 70.35%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8826 88.26%
OATP1B3 inhibitior + 0.9294 92.94%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6667 66.67%
P-glycoprotein inhibitior - 0.6914 69.14%
P-glycoprotein substrate + 0.5417 54.17%
CYP3A4 substrate + 0.6532 65.32%
CYP2C9 substrate - 0.5888 58.88%
CYP2D6 substrate - 0.8138 81.38%
CYP3A4 inhibition - 0.8671 86.71%
CYP2C9 inhibition - 0.8460 84.60%
CYP2C19 inhibition - 0.8223 82.23%
CYP2D6 inhibition - 0.9000 90.00%
CYP1A2 inhibition - 0.7366 73.66%
CYP2C8 inhibition + 0.4604 46.04%
CYP inhibitory promiscuity - 0.9124 91.24%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.8900 89.00%
Carcinogenicity (trinary) Non-required 0.5456 54.56%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9282 92.82%
Skin irritation - 0.7624 76.24%
Skin corrosion - 0.9307 93.07%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5820 58.20%
Micronuclear + 0.5300 53.00%
Hepatotoxicity - 0.6047 60.47%
skin sensitisation - 0.8114 81.14%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.6096 60.96%
Acute Oral Toxicity (c) III 0.6029 60.29%
Estrogen receptor binding + 0.7308 73.08%
Androgen receptor binding + 0.6772 67.72%
Thyroid receptor binding + 0.6458 64.58%
Glucocorticoid receptor binding + 0.8501 85.01%
Aromatase binding + 0.7670 76.70%
PPAR gamma + 0.7369 73.69%
Honey bee toxicity - 0.8003 80.03%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.9110 91.10%

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 99.31% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.23% 98.95%
CHEMBL1951 P21397 Monoamine oxidase A 94.59% 91.49%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 94.19% 95.64%
CHEMBL241 Q14432 Phosphodiesterase 3A 93.85% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.40% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.75% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.47% 95.56%
CHEMBL2850 P49840 Glycogen synthase kinase-3 alpha 90.30% 88.84%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 89.98% 92.88%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.85% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.95% 95.89%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 87.59% 85.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.06% 100.00%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 86.77% 93.40%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.35% 94.00%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 85.21% 91.03%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 84.98% 96.77%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 83.75% 94.78%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.50% 90.71%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.36% 93.03%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.53% 85.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.40% 82.69%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 80.31% 86.00%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 80.01% 95.53%

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 10069635
LOTUS LTS0000346
wikiData Q77563837