[(3aS,4S,5S,6E,10Z,11aR)-6-formyl-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-methylbutanoate

Details

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Internal ID ddc03aae-8f30-4688-a4da-315f778421e2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4S,5S,6E,10Z,11aR)-6-formyl-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1C2C(C=C(CCC=C(C1O)C=O)CO)OC(=O)C2=C
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(/CC/C=C(\[C@@H]1O)/C=O)\CO)OC(=O)C2=C
InChI InChI=1S/C20H26O7/c1-4-11(2)19(24)27-18-16-12(3)20(25)26-15(16)8-13(9-21)6-5-7-14(10-22)17(18)23/h7-8,10-11,15-18,21,23H,3-6,9H2,1-2H3/b13-8-,14-7-/t11-,15-,16+,17+,18+/m1/s1
InChI Key KZJNKSIORXDWKH-QODSFXCKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O7
Molecular Weight 378.40 g/mol
Exact Mass 378.16785316 g/mol
Topological Polar Surface Area (TPSA) 110.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.24
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4S,5S,6E,10Z,11aR)-6-formyl-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9567 95.67%
Caco-2 - 0.6994 69.94%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7385 73.85%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8361 83.61%
OATP1B3 inhibitior + 0.9549 95.49%
MATE1 inhibitior - 0.9012 90.12%
OCT2 inhibitior - 0.7570 75.70%
BSEP inhibitior - 0.9024 90.24%
P-glycoprotein inhibitior - 0.7098 70.98%
P-glycoprotein substrate - 0.6299 62.99%
CYP3A4 substrate + 0.6015 60.15%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8966 89.66%
CYP3A4 inhibition - 0.5645 56.45%
CYP2C9 inhibition - 0.6660 66.60%
CYP2C19 inhibition - 0.7228 72.28%
CYP2D6 inhibition - 0.8703 87.03%
CYP1A2 inhibition - 0.5728 57.28%
CYP2C8 inhibition - 0.6599 65.99%
CYP inhibitory promiscuity - 0.6560 65.60%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9443 94.43%
Carcinogenicity (trinary) Non-required 0.6242 62.42%
Eye corrosion - 0.9719 97.19%
Eye irritation - 0.9081 90.81%
Skin irritation - 0.6597 65.97%
Skin corrosion - 0.9281 92.81%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5073 50.73%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.5793 57.93%
skin sensitisation - 0.8495 84.95%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity - 0.7067 70.67%
Acute Oral Toxicity (c) III 0.4859 48.59%
Estrogen receptor binding + 0.5308 53.08%
Androgen receptor binding - 0.4922 49.22%
Thyroid receptor binding - 0.5637 56.37%
Glucocorticoid receptor binding + 0.6461 64.61%
Aromatase binding - 0.7493 74.93%
PPAR gamma - 0.6485 64.85%
Honey bee toxicity - 0.7839 78.39%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9789 97.89%

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 96.45% 97.25%
CHEMBL2581 P07339 Cathepsin D 95.17% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.86% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 93.07% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.85% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.58% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.29% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.86% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.23% 97.09%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 83.18% 96.47%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.86% 95.50%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 82.29% 98.75%
CHEMBL2996 Q05655 Protein kinase C delta 81.09% 97.79%

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.
Acanthospermum hispidum
Lecocarpus pinnatifidus

Cross-Links

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PubChem 98755155
LOTUS LTS0141394
wikiData Q105148184