[(4aS,5S,6R,7R,8aS)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] (1R,4S,6R,7S,11S,12R,13S,16R)-4-ethenyl-6-[2-(hydroxymethyl)prop-2-enoyloxy]-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.01,13.04,12.07,11]nonadecane-16-carboxylate

Details

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Internal ID 0810d25f-970a-455d-a6ce-ccb062164955
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name [(4aS,5S,6R,7R,8aS)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] (1R,4S,6R,7S,11S,12R,13S,16R)-4-ethenyl-6-[2-(hydroxymethyl)prop-2-enoyloxy]-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.01,13.04,12.07,11]nonadecane-16-carboxylate
SMILES (Canonical) COC(=O)C(=C)C1C(CC2(COC(=O)C(=C)C2C1O)C=C)OC(=O)C34CCC5C6C7C(C(CC6(COC5(O3)OC4)C=C)OC(=O)C(=C)CO)C(=C)C(=O)O7
SMILES (Isomeric) COC(=O)C(=C)[C@H]1[C@@H](C[C@]2(COC(=O)C(=C)[C@H]2[C@@H]1O)C=C)OC(=O)[C@]34CC[C@H]5[C@H]6[C@H]7[C@H]([C@@H](C[C@]6(CO[C@@]5(O3)OC4)C=C)OC(=O)C(=C)CO)C(=C)C(=O)O7
InChI InChI=1S/C39H44O15/c1-8-36-12-23(25(19(4)32(43)47-7)29(41)27(36)21(6)33(44)48-15-36)52-35(46)38-11-10-22-28-30-26(20(5)34(45)53-30)24(51-31(42)18(3)14-40)13-37(28,9-2)16-49-39(22,54-38)50-17-38/h8-9,22-30,40-41H,1-6,10-17H2,7H3/t22-,23+,24+,25-,26-,27-,28-,29+,30+,36-,37-,38+,39+/m0/s1
InChI Key BECRUZTUIGOWQI-RNUNKXJYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C39H44O15
Molecular Weight 752.80 g/mol
Exact Mass 752.26802069 g/mol
Topological Polar Surface Area (TPSA) 200.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 1.54
H-Bond Acceptor 15
H-Bond Donor 2
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(4aS,5S,6R,7R,8aS)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] (1R,4S,6R,7S,11S,12R,13S,16R)-4-ethenyl-6-[2-(hydroxymethyl)prop-2-enoyloxy]-8-methylidene-9-oxo-2,10,18,19-tetraoxapentacyclo[14.2.1.01,13.04,12.07,11]nonadecane-16-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8550 85.50%
Caco-2 - 0.8603 86.03%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.8352 83.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8517 85.17%
OATP1B3 inhibitior + 0.9503 95.03%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8021 80.21%
BSEP inhibitior + 0.8477 84.77%
P-glycoprotein inhibitior + 0.7510 75.10%
P-glycoprotein substrate + 0.7399 73.99%
CYP3A4 substrate + 0.7393 73.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8309 83.09%
CYP3A4 inhibition - 0.8734 87.34%
CYP2C9 inhibition - 0.8886 88.86%
CYP2C19 inhibition - 0.8029 80.29%
CYP2D6 inhibition - 0.9217 92.17%
CYP1A2 inhibition - 0.8593 85.93%
CYP2C8 inhibition + 0.7409 74.09%
CYP inhibitory promiscuity - 0.7983 79.83%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4964 49.64%
Eye corrosion - 0.9796 97.96%
Eye irritation - 0.9076 90.76%
Skin irritation - 0.7354 73.54%
Skin corrosion - 0.9351 93.51%
Ames mutagenesis - 0.5370 53.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6891 68.91%
Micronuclear - 0.7500 75.00%
Hepatotoxicity + 0.5750 57.50%
skin sensitisation - 0.8369 83.69%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.6939 69.39%
Acute Oral Toxicity (c) III 0.3930 39.30%
Estrogen receptor binding + 0.7733 77.33%
Androgen receptor binding + 0.7504 75.04%
Thyroid receptor binding + 0.5371 53.71%
Glucocorticoid receptor binding + 0.6474 64.74%
Aromatase binding + 0.6374 63.74%
PPAR gamma + 0.7134 71.34%
Honey bee toxicity - 0.6140 61.40%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9025 90.25%

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 99.57% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.26% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 91.80% 95.93%
CHEMBL2581 P07339 Cathepsin D 90.75% 98.95%
CHEMBL204 P00734 Thrombin 90.29% 96.01%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.98% 85.14%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 89.64% 91.07%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.40% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 89.38% 91.19%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.13% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.67% 97.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.76% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.69% 92.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.64% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.61% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.40% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.32% 86.33%
CHEMBL5028 O14672 ADAM10 84.25% 97.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.08% 99.23%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.94% 99.17%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 83.31% 98.75%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.46% 97.09%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.51% 97.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.12% 95.89%

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.
Baccharoides anthelmintica

Cross-Links

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PubChem 50942791
LOTUS LTS0035794
wikiData Q104932653