(3aR,4S,6aR,9aR,9bR)-Dodecahydro-3,6,9-tris(methylene)-2,8-dioxoazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)-2-propenoate

Details

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Internal ID a8dc0a76-f52e-4ea4-909b-df061e99e1ea
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4S,6aR,9aR,9bR)-3,6,9-trimethylidene-2,8-dioxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
SMILES (Canonical) C=C1CC(C2C(C3C1CC(=O)C3=C)OC(=O)C2=C)OC(=O)C(=C)CO
SMILES (Isomeric) C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1CC(=O)C3=C)OC(=O)C2=C)OC(=O)C(=C)CO
InChI InChI=1S/C19H20O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12,14-17,20H,1-7H2/t12-,14-,15-,16+,17+/m0/s1
InChI Key MSTZNVVCBOEAGA-ZZTPXLKCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C19H20O6
Molecular Weight 344.40 g/mol
Exact Mass 344.12598835 g/mol
Topological Polar Surface Area (TPSA) 89.90 Ų
XlogP 1.00
Atomic LogP (AlogP) 1.27
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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(3aR,4S,6aR,9aR,9bR)-Dodecahydro-3,6,9-tris(methylene)-2,8-dioxoazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)-2-propenoate
35821-02-4

2D Structure

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2D Structure of (3aR,4S,6aR,9aR,9bR)-Dodecahydro-3,6,9-tris(methylene)-2,8-dioxoazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)-2-propenoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9834 98.34%
Caco-2 - 0.6600 66.00%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability + 0.6429 64.29%
Subcellular localzation Mitochondria 0.6363 63.63%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9141 91.41%
OATP1B3 inhibitior + 0.9525 95.25%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8184 81.84%
P-glycoprotein inhibitior - 0.6694 66.94%
P-glycoprotein substrate - 0.6965 69.65%
CYP3A4 substrate + 0.5800 58.00%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8638 86.38%
CYP3A4 inhibition - 0.8298 82.98%
CYP2C9 inhibition - 0.8635 86.35%
CYP2C19 inhibition - 0.8189 81.89%
CYP2D6 inhibition - 0.9308 93.08%
CYP1A2 inhibition - 0.7458 74.58%
CYP2C8 inhibition - 0.8012 80.12%
CYP inhibitory promiscuity - 0.8548 85.48%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9143 91.43%
Carcinogenicity (trinary) Non-required 0.6504 65.04%
Eye corrosion - 0.9122 91.22%
Eye irritation + 0.6260 62.60%
Skin irritation - 0.6275 62.75%
Skin corrosion - 0.8740 87.40%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5845 58.45%
Micronuclear - 0.6400 64.00%
Hepatotoxicity + 0.5875 58.75%
skin sensitisation - 0.7558 75.58%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.7447 74.47%
Acute Oral Toxicity (c) III 0.4229 42.29%
Estrogen receptor binding + 0.6392 63.92%
Androgen receptor binding + 0.5674 56.74%
Thyroid receptor binding - 0.4921 49.21%
Glucocorticoid receptor binding + 0.5536 55.36%
Aromatase binding - 0.4932 49.32%
PPAR gamma + 0.5814 58.14%
Honey bee toxicity - 0.6919 69.19%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6450 64.50%
Fish aquatic toxicity + 0.9131 91.31%

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 96.45% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.05% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.99% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 81.53% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.83% 95.56%

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.
Cynara cardunculus

Cross-Links

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PubChem 12149910
LOTUS LTS0182739
wikiData Q105171417