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[(1R,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-1-hydroxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl (E)-2-methylbut-2-enoate

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 4ca30d99-a3ae-4104-8980-84e4b7a9366e
Taxonomy Organoheterocyclic compounds > Furofurans
IUPAC Name [(1R,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-1-hydroxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OCC12C(CC(C(C1C(CCC23CO3)O)(C)C4CC5CCOC5O4)C)OC(=O)C
SMILES (Isomeric) C/C=C(\C)/C(=O)OC[C@@]12[C@H](C[C@H]([C@]([C@H]1[C@@H](CC[C@]23CO3)O)(C)[C@@H]4C[C@H]5CCO[C@H]5O4)C)OC(=O)C
InChI InChI=1S/C27H40O8/c1-6-15(2)23(30)32-14-27-21(34-17(4)28)11-16(3)25(5,20-12-18-8-10-31-24(18)35-20)22(27)19(29)7-9-26(27)13-33-26/h6,16,18-22,24,29H,7-14H2,1-5H3/b15-6+/t16-,18-,19-,20+,21+,22-,24+,25-,26+,27-/m1/s1
InChI Key BYLZDSBPRYUCTF-UYIDWTRYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H40O8
Molecular Weight 492.60 g/mol
Exact Mass 492.27231823 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.15
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-1-hydroxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl (E)-2-methylbut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9854 98.54%
Caco-2 - 0.6577 65.77%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.8449 84.49%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8486 84.86%
OATP1B3 inhibitior + 0.9401 94.01%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.8148 81.48%
P-glycoprotein inhibitior + 0.6320 63.20%
P-glycoprotein substrate + 0.5366 53.66%
CYP3A4 substrate + 0.7175 71.75%
CYP2C9 substrate - 0.8110 81.10%
CYP2D6 substrate - 0.8926 89.26%
CYP3A4 inhibition - 0.7102 71.02%
CYP2C9 inhibition - 0.7230 72.30%
CYP2C19 inhibition - 0.8387 83.87%
CYP2D6 inhibition - 0.9434 94.34%
CYP1A2 inhibition - 0.8740 87.40%
CYP2C8 inhibition + 0.6221 62.21%
CYP inhibitory promiscuity - 0.8760 87.60%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5044 50.44%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9373 93.73%
Skin irritation - 0.5626 56.26%
Skin corrosion - 0.9359 93.59%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4179 41.79%
Micronuclear - 0.6600 66.00%
Hepatotoxicity - 0.6000 60.00%
skin sensitisation - 0.8899 88.99%
Respiratory toxicity - 0.5889 58.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.4502 45.02%
Acute Oral Toxicity (c) I 0.6613 66.13%
Estrogen receptor binding + 0.8824 88.24%
Androgen receptor binding + 0.6845 68.45%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7790 77.90%
Aromatase binding + 0.7762 77.62%
PPAR gamma + 0.7061 70.61%
Honey bee toxicity - 0.7086 70.86%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9917 99.17%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.93% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.94% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.50% 97.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 93.32% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.20% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 89.40% 91.19%
CHEMBL241 Q14432 Phosphodiesterase 3A 88.69% 92.94%
CHEMBL2581 P07339 Cathepsin D 88.44% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.82% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.67% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.37% 97.25%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 87.11% 95.58%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.05% 91.07%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 86.73% 98.75%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 86.71% 94.80%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.58% 96.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.54% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 84.66% 90.17%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 84.21% 89.05%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 83.34% 89.34%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 82.94% 91.24%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.78% 95.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.59% 100.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.28% 97.28%
CHEMBL5028 O14672 ADAM10 82.11% 97.50%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.60% 93.00%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 81.39% 100.00%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 81.08% 98.99%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.59% 94.33%

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.
Ajuga genevensis

Cross-Links

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PubChem 101619547
LOTUS LTS0237538
wikiData Q104949522