[(3S,4R,4aR,5R,7S,8S,8aS)-8-[2-(furan-3-yl)ethyl]-3,5,8a-trihydroxy-7,8-dimethyl-6-oxospiro[2,3,5,7-tetrahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate

Details

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Internal ID 623d24f5-2bc5-4b16-a69f-72e1505e6b37
Taxonomy Organoheterocyclic compounds > Heteroaromatic compounds
IUPAC Name [(3S,4R,4aR,5R,7S,8S,8aS)-8-[2-(furan-3-yl)ethyl]-3,5,8a-trihydroxy-7,8-dimethyl-6-oxospiro[2,3,5,7-tetrahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
SMILES (Canonical) CC1C(=O)C(C2(C(C1(C)CCC3=COC=C3)(CCC(C24CO4)O)O)COC(=O)C)O
SMILES (Isomeric) C[C@@H]1C(=O)[C@@H]([C@@]2([C@@]([C@@]1(C)CCC3=COC=C3)(CC[C@@H]([C@]24CO4)O)O)COC(=O)C)O
InChI InChI=1S/C22H30O8/c1-13-17(25)18(26)20(11-29-14(2)23)21(12-30-21)16(24)5-8-22(20,27)19(13,3)7-4-15-6-9-28-10-15/h6,9-10,13,16,18,24,26-27H,4-5,7-8,11-12H2,1-3H3/t13-,16+,18+,19+,20+,21-,22+/m1/s1
InChI Key WXSHKWVQZSHQBD-AWVSDTHSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O8
Molecular Weight 422.50 g/mol
Exact Mass 422.19406791 g/mol
Topological Polar Surface Area (TPSA) 130.00 Ų
XlogP 0.30
Atomic LogP (AlogP) 1.00
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3S,4R,4aR,5R,7S,8S,8aS)-8-[2-(furan-3-yl)ethyl]-3,5,8a-trihydroxy-7,8-dimethyl-6-oxospiro[2,3,5,7-tetrahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8910 89.10%
Caco-2 - 0.7041 70.41%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7302 73.02%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7406 74.06%
OATP1B3 inhibitior + 0.9315 93.15%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.8514 85.14%
P-glycoprotein inhibitior - 0.5645 56.45%
P-glycoprotein substrate + 0.6499 64.99%
CYP3A4 substrate + 0.7104 71.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8260 82.60%
CYP3A4 inhibition - 0.5343 53.43%
CYP2C9 inhibition - 0.7369 73.69%
CYP2C19 inhibition - 0.7801 78.01%
CYP2D6 inhibition - 0.9454 94.54%
CYP1A2 inhibition - 0.8976 89.76%
CYP2C8 inhibition + 0.5281 52.81%
CYP inhibitory promiscuity - 0.9049 90.49%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5375 53.75%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9569 95.69%
Skin irritation - 0.6652 66.52%
Skin corrosion - 0.9435 94.35%
Ames mutagenesis - 0.6540 65.40%
Human Ether-a-go-go-Related Gene inhibition + 0.7154 71.54%
Micronuclear - 0.7100 71.00%
Hepatotoxicity + 0.5234 52.34%
skin sensitisation - 0.9221 92.21%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.6929 69.29%
Acute Oral Toxicity (c) I 0.5387 53.87%
Estrogen receptor binding + 0.8594 85.94%
Androgen receptor binding + 0.7475 74.75%
Thyroid receptor binding + 0.5442 54.42%
Glucocorticoid receptor binding + 0.8172 81.72%
Aromatase binding + 0.7309 73.09%
PPAR gamma + 0.5319 53.19%
Honey bee toxicity - 0.7969 79.69%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5250 52.50%
Fish aquatic toxicity + 0.9794 97.94%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.44% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.47% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.94% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.44% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.62% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.01% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.44% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.13% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.27% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.29% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.22% 85.14%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 85.38% 94.80%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.22% 82.69%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.19% 100.00%
CHEMBL4040 P28482 MAP kinase ERK2 84.88% 83.82%
CHEMBL3922 P50579 Methionine aminopeptidase 2 84.54% 97.28%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.44% 93.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.58% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.13% 94.00%

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.
Teucrium oliverianum
Teucrium orientale

Cross-Links

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PubChem 163086778
LOTUS LTS0158179
wikiData Q105314896