(1S)-2alpha-(Benzoyloxy)-4alpha-acetoxy-7beta,9alpha-[[(S)-4-hydroxybenzylidene]bisoxy]-5beta,20-epoxy-1,11-cyclo-11,15-secotaxa-11-ene-10beta,13alpha,15-triol

Details

Top
Internal ID b8ef55b4-d425-4266-9fde-f65bf0f27c3b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name [(1R,2S,5R,7S,9S,11R,12R,15S,17S,18S,19S)-2-acetyloxy-12,15-dihydroxy-9-(4-hydroxyphenyl)-17-(2-hydroxypropan-2-yl)-14,19-dimethyl-4,8,10-trioxapentacyclo[9.7.1.02,5.07,19.013,17]nonadec-13-en-18-yl] benzoate
SMILES (Canonical) CC1=C2C(C3C4(C(CC5C(C4C(C2(CC1O)C(C)(C)O)OC(=O)C6=CC=CC=C6)(CO5)OC(=O)C)OC(O3)C7=CC=C(C=C7)O)C)O
SMILES (Isomeric) CC1=C2[C@H]([C@H]3[C@@]4([C@H](C[C@@H]5[C@]([C@H]4[C@@H]([C@@]2(C[C@@H]1O)C(C)(C)O)OC(=O)C6=CC=CC=C6)(CO5)OC(=O)C)O[C@@H](O3)C7=CC=C(C=C7)O)C)O
InChI InChI=1S/C36H42O11/c1-18-23(39)16-35(33(3,4)42)26(18)27(40)29-34(5)24(44-32(46-29)21-11-13-22(38)14-12-21)15-25-36(17-43-25,47-19(2)37)28(34)30(35)45-31(41)20-9-7-6-8-10-20/h6-14,23-25,27-30,32,38-40,42H,15-17H2,1-5H3/t23-,24-,25+,27+,28-,29-,30-,32-,34+,35-,36-/m0/s1
InChI Key AVBFIJHUOKVCCJ-MMJDANQTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C36H42O11
Molecular Weight 650.70 g/mol
Exact Mass 650.27271215 g/mol
Topological Polar Surface Area (TPSA) 161.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 3.34
H-Bond Acceptor 11
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (1S)-2alpha-(Benzoyloxy)-4alpha-acetoxy-7beta,9alpha-[[(S)-4-hydroxybenzylidene]bisoxy]-5beta,20-epoxy-1,11-cyclo-11,15-secotaxa-11-ene-10beta,13alpha,15-triol

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9784 97.84%
Caco-2 - 0.8257 82.57%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7893 78.93%
OATP2B1 inhibitior - 0.8595 85.95%
OATP1B1 inhibitior + 0.8020 80.20%
OATP1B3 inhibitior + 0.9113 91.13%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9177 91.77%
P-glycoprotein inhibitior + 0.7685 76.85%
P-glycoprotein substrate + 0.7523 75.23%
CYP3A4 substrate + 0.7211 72.11%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8718 87.18%
CYP3A4 inhibition - 0.6785 67.85%
CYP2C9 inhibition - 0.6568 65.68%
CYP2C19 inhibition - 0.7269 72.69%
CYP2D6 inhibition - 0.8959 89.59%
CYP1A2 inhibition - 0.7617 76.17%
CYP2C8 inhibition + 0.8848 88.48%
CYP inhibitory promiscuity - 0.8285 82.85%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4602 46.02%
Eye corrosion - 0.9867 98.67%
Eye irritation - 0.9054 90.54%
Skin irritation - 0.7104 71.04%
Skin corrosion - 0.9288 92.88%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8203 82.03%
Micronuclear + 0.5400 54.00%
Hepatotoxicity + 0.5597 55.97%
skin sensitisation - 0.8115 81.15%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity + 0.7844 78.44%
Acute Oral Toxicity (c) I 0.4381 43.81%
Estrogen receptor binding + 0.8013 80.13%
Androgen receptor binding + 0.7562 75.62%
Thyroid receptor binding + 0.5992 59.92%
Glucocorticoid receptor binding + 0.7310 73.10%
Aromatase binding + 0.6717 67.17%
PPAR gamma + 0.7119 71.19%
Honey bee toxicity - 0.6562 65.62%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6300 63.00%
Fish aquatic toxicity + 0.9962 99.62%

Targets

Top

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
CHEMBL1951 P21397 Monoamine oxidase A 98.01% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.04% 86.33%
CHEMBL2581 P07339 Cathepsin D 96.31% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.70% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.63% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.16% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.23% 95.56%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 91.65% 94.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.07% 99.23%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 90.64% 90.93%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.62% 97.14%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 88.25% 89.44%
CHEMBL340 P08684 Cytochrome P450 3A4 86.92% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.73% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 86.12% 94.73%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.80% 96.95%
CHEMBL5028 O14672 ADAM10 83.74% 97.50%
CHEMBL2535 P11166 Glucose transporter 82.88% 98.75%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.79% 95.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.06% 99.17%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 82.00% 94.08%
CHEMBL2996 Q05655 Protein kinase C delta 81.72% 97.79%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 80.77% 83.00%

Plants that contains it

Top
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.
Equisetum hyemale

Cross-Links

Top
PubChem 44233385
NPASS NPC206226